Ammonia → HCID 178481486, compound

HRID 840163Notes

Reaction equation

HRID 840163 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:21]2[CH:22]=[C:23]3[C:28](=[CH:29][CH:30]=2)[N:27]([CH3:31])[C:26](=[O:32])[CH:25]=[C:24]3[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([OH:20])[C:9]2[N:10]=[CH:11][N:12](S(N(C)C)(=O)=[O:15])[CH:13]=2)=[CH:4][CH:3]=1.N>Cl.O.CO>[OH2:15].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:20])([C:9]2[N:10]=[CH:11][NH:12][CH:13]=2)[C:21]2[CH:22]=[C:23]3[C:28](=[CH:29][CH:30]=2)[N:27]([CH3:31])[C:26](=[O:32])[CH:25]=[C:24]3[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 222AmmoniaHCID 22714362(+)-4-[(4-chlorophenyl)(1,2-dihydro-1-methyl-2-oxo-4-phenyl-6-quinolinyl)hydroxymethyl]-N,N-dimethyl-1H-imidazole-1-sulfonamide

Product 1

HCID 178481486HCID 178481486, compoundYield 49.7%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of (±)-4-[(4-chlorophenyl)(1,2-dihydro-1-methyl-2-oxo-4-phenyl-6-quinolinyl)hydroxymethyl]-N,N-dimethyl-1H-imidazole-1-sulfonamide (2.4 g) in hydrochloric acid (10 ml), water (30 ml) and methanol (15 ml) was stirred and heated at 110° C. for 14 hours. The mixture was cooled, basified with NH3 (aq.) and extracted with DCM. The organic layer was dried, filtered off and evaporated till dryness. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 95/5/0.2). The pure fractions were collected and evaporated. The residue (1.25 g) was crystallized from 2-propanone/DIPE, yielding 1 g (48.3%) of (±)-6-[(4-chlorophenyl)hydroxy(1H-imidazol-4-yl)methyl]-1-methyl-4-phenyl-2(1H)-quinolinone monohydrate (comp. 43).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with DCM
  3. customThe organic layer was dried
  4. filtrationfiltered off
  5. customevaporated till dryness
  6. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 95/5/0.2)
  7. customThe pure fractions were collected
  8. customevaporated
  9. customThe residue (1.25 g) was crystallized from 2-propanone/DIPE

Sources & evidence

ORD record
ord-af01752b38bd416d8640f86397e2aff6
Source dataset
uspto-grants-2002_04
Patent number
US06365600B1

Reaction notes

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