Hydrochloric Acid → HCID 3032237, compound

HRID 1462902Notes

Reaction equation

HRID 1462902 reaction equation
C1(NC2CCCCC2)CCCCC1.[C:14]([S:22][CH2:23][CH2:24][C:25]([N:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:30][CH2:29][CH:28]1[C:37]([OH:39])=[O:38])=[O:26])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl>CC(O)C>[C:14]([S:22][CH2:23][CH2:24][C:25]([N:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:30][CH2:29][CH:28]1[C:37]([OH:39])=[O:38])=[O:26])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86739569HCID 86739569, compound

Product 1

HCID 3032237HCID 3032237, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

The (±)-1-(3-benzoylthio-1-oxopropyl)-1,2,3,4-tetrahydro-2-quinolinecarboxylic acid dicyclohexylamine salt thus obtained (35.6 g) was suspended in 2-propanol (200 ml) and this mixture was treated with a solution of dry hydrogen chloride in 2-propanol (27 ml) with cooling in an ice bath. The resulting dicyclohexylamine hydrochloride was filtered and washed twice with 2-propanol (20 ml). The combined filtrate and washings were concentrated under reduced pressure. The residue was dissolved in ether (300 ml) and this solution was dried over sodium sulfate and concentrated under reduced pressure to give 23.6 g of (±)-1-(3-benzoylthio-1-oxopropyl)-1,2,3,4-tetrahydro-2-quinolinecarboxylic acid, m.p. 99°-101°.

Workup

  1. temperaturewith cooling in an ice bath
  2. filtrationThe resulting dicyclohexylamine hydrochloride was filtered
  3. washwashed twice with 2-propanol (20 ml)
  4. concentrationThe combined filtrate and washings were concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in ether (300 ml)
  6. dry with materialthis solution was dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b17dbf722d34426ea3f13dafc9ff6d5b
Source dataset
uspto-grants-1984_07
Patent number
US04461896

Reaction notes

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