Diisopropylethylamine → 4-Nitrophenyl (7-chloro-4-oxo-1-phenyl-1,4-dihydroquinolin-3-yl)methylcarbamate

HRID 1887829Notes

Reaction equation

HRID 1887829 reaction equation
[NH2:1][CH2:2][C:3]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][C:8]([Cl:14])=[CH:9][CH:10]=2)[N:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:4]=1.Cl[C:22]([O:24][C:25]1[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=1)=[O:23].C(N(CC)C(C)C)(C)C>C(Cl)Cl>[N+:31]([C:28]1[CH:27]=[CH:26][C:25]([O:24][C:22](=[O:23])[NH:1][CH2:2][C:3]2[C:12](=[O:13])[C:11]3[C:6](=[CH:7][C:8]([Cl:14])=[CH:9][CH:10]=3)[N:5]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:4]=2)=[CH:30][CH:29]=1)([O-:33])=[O:32]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 712083983-(aminomethyl)-7-chloro-1-phenylquinolin-4(1H)-one2×

Product 1

HCID 866757694-Nitrophenyl (7-chloro-4-oxo-1-phenyl-1,4-dihydroquinolin-3-yl)methylcarbamateYield 101.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 250 mL round-bottomed flask, 3-(aminomethyl)-7-chloro-1-phenylquinolin-4(1H)-one (intermediate D) (1 g, 3.51 mmol), 4-nitrophenyl chloroformate (708 mg, 3.51 mmol) and N,N-diisopropylethylamine (1.36 g, 1.84 mL, 10.5 mmol) were combined with CH2Cl2 (30 mL). The reaction mixture was stirred overnight at room temperature. After this time, the reaction mixture was concentrated to dryness to afford (7-chloro-4-oxo-1-phenyl-1,4-dihydro-quinolin-3-ylmethyl)-carbamic acid 4-nitro-phenyl ester (1.6 g, 100%)

Workup

  1. concentrationAfter this time, the reaction mixture was concentrated to dryness

Sources & evidence

ORD record
ord-ca8ef436e2074fc88b1f15c70afebf38
Source dataset
uspto-grants-2013_08
Patent number
US08501732B2

Reaction notes

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