Formamide → (+/-)-N-[(4-chlorophenyl)-(1,2-dihydro-1-methyl-2-oxo-4-phenyl-6-quinolinyl)methyl]formamide

HRID 1739816Notes

Reaction equation

[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([C:6]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH3:18])[C:13](=[O:19])[CH:12]=[C:11]3[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=O)=[CH:4][CH:3]=1.[CH:28]([NH2:30])=[O:29]>C(O)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH3:18])[C:13](=[O:19])[CH:12]=[C:11]3[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[NH:30][CH:28]=[O:29])=[CH:26][CH:27]=1

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of 6-(4-chlorobenzoyl)-1-methyl-4-phenyl-2(1H)-quinolinone (24 g) in formamide (130 ml) and formic acid (100 ml) was stirred and heated at 160° C. for 12 hours. The mixture was poured into ice water and extracted with DCM. The organic layer was dried (MgSO4), filtered off and evaporated till dryness. The product was used without further purification, yielding 24.2 g (93%) of (±)-N-[(4-chlorophenyl)-(1,2-dihydro-1-methyl-2-oxo-4-phenyl-6-quinolinyl)methyl]formamide (interm. 5-a).

Workup

extractionextracted with DCM
dry with materialThe organic layer was dried (MgSO4)
filtrationfiltered off
customevaporated till dryness
customThe product was used without further purification

Sources & evidence

ORD record: ord-1c58bfbf09554677a3db4398dadbf51b
Source dataset: uspto-grants-1999_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05968952

Reaction notes

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