Hydrochloric Acid → HCID 13750926, compound

HRID 1886135Notes

Reaction equation

HRID 1886135 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=2)[CH2:5][CH2:4][CH2:3]1.[ClH:13].[N:14]([O-])=[O:15].[Na+].CCOCC>O>[ClH:13].[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]([N:14]=[O:15])=[C:9]([OH:12])[CH:10]=2)[CH2:5][CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 137509151-Methyl-1,2,3,4-tetrahydroquinolin-7-olHCID 23668193Sodium Nitrite

Product 1

HCID 13750926HCID 13750926, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
4 °C

Procedure

A mixture of 24.5 g (0.15 mol) of 1-methyl-1,2,3,4-tetrahydro-7-hydroxyquinoline, 75 ml of water and 75 ml of concentrated hydrochloric acid was stirred and cooled in an ice bath to 5°. To this mixture was added dropwise during 40 minutes a solution of 12.42 g(0.18 mol) of sodium nitrite in 50 ml of water while maintaining the temperature between 3 to 5° C. It was occasionally necessary to add a few ml of ether to control foaming. When the addition was complete, the reaction mixture was stirred for 40 min in the ice bath. The solid was collected and rinsed with 2N hydrochloric acid and with ether. It was recrystallized from 700 ml of 2.4 N hydrochloric acid to give 28.7 g (84%) of crude product as brown needles.

Workup

  1. temperaturecooled in an ice bath to 5°
  2. additionWhen the addition
  3. customThe solid was collected
  4. washrinsed with 2N hydrochloric acid and with ether
  5. customIt was recrystallized from 700 ml of 2.4 N hydrochloric acid

Sources & evidence

ORD record
ord-202cda55811643f18090eab31ecb9100
Source dataset
uspto-grants-1992_09
Patent number
US05149807

Reaction notes

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