Ammonium Hydroxide → (+/-)-6-[amino-(4-chlorophenyl)methyl]-1-methyl-4-phenyl-2(1H)-quinolinone

HRID 1739817Notes

Reaction equation

HRID 1739817 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[N:18]([CH3:22])[C:17](=[O:23])[CH:16]=[C:15]3[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[NH:9]C=O)=[CH:4][CH:3]=1.[NH4+].[OH-]>Cl.CC(O)C>[NH2:9][CH:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[N:18]([CH3:22])[C:17](=[O:23])[CH:16]=[C:15]2[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 21837469(+/-)-N-[(4-chlorophenyl)-(1,2-dihydro-1-methyl-2-oxo-4-phenyl-6-quinolinyl)methyl]formamide

Product 1

HCID 21837488(+/-)-6-[amino-(4-chlorophenyl)methyl]-1-methyl-4-phenyl-2(1H)-quinolinoneYield 59%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3776IsopropanolSolvent

Procedure

A mixture of intermediate (5-a) (21.2 g) in hydrochloric acid (3 N) (150 ml) and 2-propanol (150 ml) was stirred and refluxed overnight. The mixture was poured into ice, basified with NH4OH and extracted with DCM. The organic layer was dried (MgSO4), filtered off and evaporated till dryness. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH/NH4OH 98/2/0.1). The pure fractions were collected and evaporated, yielding 11.6 g (59%) of (±)-6-[amino-(4-chlorophenyl)methyl]-1-methyl-4-phenyl-2(1H)-quinolinone (interm. 5-b).

Workup

  1. temperaturerefluxed overnight
  2. additionThe mixture was poured into ice
  3. extractionextracted with DCM
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered off
  6. customevaporated till dryness
  7. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH/NH4OH 98/2/0.1)
  8. customThe pure fractions were collected
  9. customevaporated

Sources & evidence

ORD record
ord-a674ccb48a5d4b42b4843a2f5f4e2b6d
Source dataset
uspto-grants-1999_10
Patent number
US05968952

Reaction notes

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