Ammonium Hydroxide → EU 5031

HRID 1462906Notes

Reaction equation

HRID 1462906 reaction equation
C([S:9][CH2:10][CH2:11][C:12]([N:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][CH2:16][C@H:15]1[C:24]([OH:26])=[O:25])=[O:13])(=O)C1C=CC=CC=1.[OH-].[NH4+]>O>[SH:9][CH2:10][CH2:11][C:12]([N:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][CH2:16][C@H:15]1[C:24]([OH:26])=[O:25])=[O:13]

Participants

4

Reactant 2

HCID 14923Ammonium Hydroxide2×HCID 13336744HCID 13336744, compound

Product 1

HCID 194686EU 5031

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

(S)(-)-(3-Benzoylthio-1-oxopropyl)-1,2,3,4-tetrahydro-2-quinolinecarboxylic acid (3 g), concentrated ammonium hydroxide (18 ml), and water (36 ml) were combined and stirred at 40°-45° under nitrogen for three hours. After this time, another portion of concentrated ammonium hydroxide (6 ml) was added and the solution was heated at 40°-45° for an additional three hours under nitrogen. The reaction mixture was then diluted with water (100 ml) and extracted well with ethyl acetate. The aqueous phase was then cooled in an ice bath and the pH adjusted to 2 with concentrated hydrochloric acid. The product was extracted with ether. The extract was dried over sodium sulfate and concentrated under reduced pressure to yield (S)(-)-1,2,3,4-tetrahydro-1-(3-mercapto-1-oxopropyl)-2-quinolinecarboxylic acid; yield 1.6 g, m.p. 130°-132°, [α]D20 -302.3° (c 1, methanol).

Workup

  1. temperaturethe solution was heated at 40°-45° for an additional three hours under nitrogen
  2. extractionextracted well with ethyl acetate
  3. temperatureThe aqueous phase was then cooled in an ice bath
  4. extractionThe product was extracted with ether
  5. dry with materialThe extract was dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-64c2aa78e7e744e9a67b841c5834dd06
Source dataset
uspto-grants-1984_07
Patent number
US04461896

Reaction notes

Loading…