Hydrochloric Acid → HCID 11553721, compound

HRID 218337Notes

Reaction equation

HRID 218337 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[CH2:12][CH3:13])[CH2:8][CH:7]([NH:14][CH2:15][C@@H:16]([C:18]1[CH:27]=[CH:26][C:25]([OH:28])=[C:24]3[C:19]=1[CH:20]=[CH:21][C:22](=[O:29])[NH:23]3)[OH:17])[CH2:6]2)[CH3:2].[ClH:30]>CO>[ClH:30].[CH2:12]([C:11]1[CH:10]=[C:9]2[C:5](=[CH:4][C:3]=1[CH2:1][CH3:2])[CH2:6][CH:7]([NH:14][CH2:15][C@@H:16]([C:18]1[CH:27]=[CH:26][C:25]([OH:28])=[C:24]3[C:19]=1[CH:20]=[CH:21][C:22](=[O:29])[NH:23]3)[OH:17])[CH2:8]2)[CH3:13]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 6918554Indacaterol

Product 1

HCID 11553721HCID 11553721, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
50 °C

Procedure

A suspension of 3.78 g (R)-5-[2-(5,6-diethyl-indan-2-ylamino)-1-hydroxyethyl]-8-hydroxy-1H-quinolin-2-one base (9.63 mmoles) in 36.5 ml methanol is heated to 50° C. A solution of 0.949 g hydrochloric acid 37% (9.63 mmoles) in 10 ml methanol is added dropwise, over 15 minutes. The resulting clear solution is allowed to cool. Crystallization begins spontaneously at 40° C. The suspension is stirred at room temperature for 17 hours. After filtration the salt is washed with 7 ml methanol. The crystals are dried for 16 hours at 50° C./ca. 10 mbar and for 2 hours at 50° C. and ca. 1 mbar. Yield: 2.33 g white powder (84.27%)

Workup

  1. temperatureto cool
  2. customCrystallization
  3. custombegins spontaneously at 40° C
  4. filtrationAfter filtration the salt
  5. washis washed with 7 ml methanol
  6. customThe crystals are dried for 16 hours at 50° C./ca. 10 mbar
  7. waitfor 2 hours at 50° C.

Sources & evidence

ORD record
ord-199190389c9445dc85fe2c47b0f8ca67
Source dataset
uspto-grants-2012_06
Patent number
US08198450B2

Reaction notes

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