Methane → 1000210-66-1

HRID 1672372Notes

Reaction equation

HRID 1672372 reaction equation
C([OH:3])C.[ClH:4].Cl.[NH2:6][CH2:7][CH2:8][S:9]([C:12]1[CH:21]=[C:20]([C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=2)[CH:19]=[C:18]2[C:13]=1[CH:14]=[CH:15][N:16]=[CH:17]2)(=[O:11])=[O:10].[OH-].[Na+].C>O>[OH2:3].[ClH:4].[NH2:6][CH2:7][CH2:8][S:9]([C:12]1[CH:21]=[C:20]([C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=2)[CH:19]=[C:18]2[C:13]=1[CH:14]=[CH:15][N:16]=[CH:17]2)(=[O:10])=[O:11].[NH2:6][CH2:7][CH2:8][S:9]([C:12]1[CH:21]=[C:20]([C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=2)[CH:19]=[C:18]2[C:13]=1[CH:14]=[CH:15][N:16]=[CH:17]2)(=[O:10])=[O:11].[ClH:4]

Participants

6

Reactant 4

HCID 297Methane3×HCID 702EthanolHCID 14798Sodium HydroxideHCID 236584011000210-63-8

Product 1

HCID 673305031000210-66-1Yield 68.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

Ethanol (8 L) and 4-[5-(2-amino-ethanesulfonyl)-isoquinolin-7-yl]-phenol di-hydrochloride salt (841.6 g; 2.097 moles) are charged to a 22 L flask equipped with overhead stirring, condenser, nitrogen inlet, heating mantle, thermocouple, and addition funnel. The 4-[5-(2-amino-ethanesulfonyl)-isoquinolin-7-yl]-phenol di-hydrochloride salt is rinsed in with ethanol (3.28 L). The reaction is warmed to 55° C. Sodium hydroxide solution (1100 mL; 1.91 N; 2.10 moles) is added to the reaction over 7 minutes during which time the temperature increases to 62° C. The reaction is heated to reflux (78° C.) and held for 1 hr. Water (1.96 L) is added to the reaction at once. The temperature decreases to 68° C. The reaction is heated back to reflux (79° C.) and a solution forms. Darco G-60® (438 g) is added to the reaction. The reaction is held at reflux for 1.25 hours. The hot Darco G-60® slurry is filtered through GFF paper into another 22 L flask. A light yellow solution results. The original flask and Darco G-60® filter cake are rinsed with hot ethanol (2.5 L). During the rinse, solid begins to form in the filtrate. The 22 L flask containing the filtrate and wash is equipped with overhead stirring, nitrogen inlet, and a thermocouple. The slurry is stirred and allowed to cool to ambient temperature. The solid is filtered and washed with ethanol (2 L). The wet cake weight is 672 g. The solid is dried in vacuo at 50° C. to give 540 g (68.9% yield) of 4-[5-(2-amino-ethanesulfonyl)-isoquinolin-7-yl]-phenol monohydrochloride hemihydrate. Mass Spectrum (LCMS) m/z=329.3) (M+H+).

Workup

  1. customequipped with overhead stirring, condenser, nitrogen inlet
  2. temperatureheating mantle
  3. additionthermocouple, and addition funnel
  4. washThe 4-[5-(2-amino-ethanesulfonyl)-isoquinolin-7-yl]-phenol di-hydrochloride salt is rinsed in with ethanol (3.28 L)
  5. temperatureincreases to 62° C
  6. temperatureThe reaction is heated
  7. temperatureto reflux (78° C.)
  8. customdecreases to 68° C
  9. temperatureThe reaction is heated back
  10. temperatureto reflux (79° C.)
  11. temperatureat reflux for 1.25 hours
  12. filtration® slurry is filtered through GFF paper into another 22 L flask
  13. customA light yellow solution results
  14. filtration® filter cake
  15. washare rinsed with hot ethanol (2.5 L)
  16. customto form in the filtrate
  17. additionThe 22 L flask containing the filtrate
  18. washwash
  19. customis equipped with overhead stirring, nitrogen inlet
  20. temperatureto cool to ambient temperature
  21. filtrationThe solid is filtered
  22. washwashed with ethanol (2 L)
  23. customThe solid is dried in vacuo at 50° C.

Sources & evidence

ORD record
ord-aca4af4b3e2840deb5d2deec29ac895a
Source dataset
uspto-grants-2011_08
Patent number
US07998977B2

Reaction notes

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