Hydrochloric Acid → HCID 13336757, compound

HRID 1462910Notes

Reaction equation

HRID 1462910 reaction equation
C([S:4][CH2:5][CH:6]([CH3:22])[C:7]([N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][CH:10]1[C:19]([OH:21])=[O:20])=[O:8])(=O)C.[OH-].[NH4+].Cl>O>[SH:4][CH2:5][CH:6]([CH3:22])[C:7]([N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][CH:10]1[C:19]([OH:21])=[O:20])=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 13336753HCID 13336753, compound

Product 1

HCID 13336757HCID 13336757, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(±) 1-(3-Acetylthio-2-methyl-1-oxopropyl)-1,2,3,4-tetrahydro-2-quinolinecarboxylic acid (26 g), concentrated ammonium hydroxide (55 ml), and water (110 ml) were combined and stirred at room temperature under nitrogen for six hours. After this time, concentrated hydrochloric acid was added while cooling with an ice bath until pH 2. The reaction mixture was extracted with ether (150 ml) and the extract dried over sodium sulfate, and evaporated to an oil. This residue, (±)-1,2,3,4-tetrahydro-1-(3-mercapto-2-methyl-1-oxopropyl)-2-quinolinecarboxylic acid, was crystallized from toluene; yield 4.5 g, m.p. 98°-101°.

Workup

  1. temperaturewhile cooling with an ice bath until pH 2
  2. extractionThe reaction mixture was extracted with ether (150 ml)
  3. dry with materialthe extract dried over sodium sulfate
  4. customevaporated to an oil
  5. customThis residue, (±)-1,2,3,4-tetrahydro-1-(3-mercapto-2-methyl-1-oxopropyl)-2-quinolinecarboxylic acid, was crystallized from toluene

Sources & evidence

ORD record
ord-73e46b60761b4d0186d1eae6e0d8026c
Source dataset
uspto-grants-1984_07
Patent number
US04461896

Reaction notes

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