Ammonium Hydroxide → (+/-)-1-(2-Mercapto-1-oxopropyl)-1,2,3,4-tetrahydro-2-quinolinecarboxylic Acid

HRID 1462914Notes

Reaction equation

HRID 1462914 reaction equation
C([S:9][CH:10]([CH3:26])[C:11]([N:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15][CH:14]1[C:23]([OH:25])=[O:24])=[O:12])(=O)C1C=CC=CC=1.[OH-].[NH4+]>O>[SH:9][CH:10]([CH3:26])[C:11]([N:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15][CH:14]1[C:23]([OH:25])=[O:24])=[O:12]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 133367612-Quinolinecarboxylic acid,1-[2-(benzoylthio)-1-oxopropyl]-1,2,3,4-tetrahydro-

Product 1

HCID 13336762(+/-)-1-(2-Mercapto-1-oxopropyl)-1,2,3,4-tetrahydro-2-quinolinecarboxylic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(±)-1-(2-Benzoylthio-1-oxopropyl)-1,2,3,4-tetrahydro-2-quinolinecarboxylic acid (4.5 g), concentrated ammonium hydroxide (8 ml) and water (16 ml) were combined and stirred at room temperature under nitrogen for three hours. The benzamide was filtered and the filtrate diluted with water (25 ml). The reaction mixture was then extracted with ethyl acetate and acidified with concentrated hydrochloric acid. The product was extracted with chloroform and the chloroform extracts dried over sodium sulfate and activated charcoal, and concentrated in vacuo. The residue, (±)-1-(2-mercapto-1-oxopropyl)-1,2,3,4-tetrahydro-2-quinolinecarboxylic acid, was triturated with carbon tetrachloride (20 ml); yield 3.2 g, m.p. 141°-143°.

Workup

  1. filtrationThe benzamide was filtered
  2. additionthe filtrate diluted with water (25 ml)
  3. extractionThe reaction mixture was then extracted with ethyl acetate
  4. extractionThe product was extracted with chloroform
  5. dry with materialthe chloroform extracts dried over sodium sulfate and activated charcoal
  6. concentrationconcentrated in vacuo
  7. customThe residue, (±)-1-(2-mercapto-1-oxopropyl)-1,2,3,4-tetrahydro-2-quinolinecarboxylic acid, was triturated with carbon tetrachloride (20 ml)

Sources & evidence

ORD record
ord-b933a63afc164801be42eed3a391cf2c
Source dataset
uspto-grants-1984_07
Patent number
US04461896

Reaction notes

Loading…