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Carbon Dioxide → 4-[(3-Bromophenyl)amino]-8-dimethylaminomethyl-6-nitro-3-quinolinecarbonitrile

HRID 612058
Notes
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Reaction equation

HRID 612058 reaction equation
[CH3:1][NH:2][CH3:3].Br[CH2:5][C:6]1[CH:7]=[C:8]([N+:29]([O-:31])=[O:30])[CH:9]=[C:10]2[C:15]=1[N:14]=[CH:13][C:12]([C:16]#[N:17])=[C:11]2[N:18]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([Br:28])[CH:23]=1)C(=O)C.C(=O)([O-])[O-].[K+].[K+].C(=O)=O>C1COCC1.CO>[Br:28][C:24]1[CH:23]=[C:22]([NH:18][C:11]2[C:10]3[C:15](=[C:6]([CH2:5][N:2]([CH3:3])[CH3:1])[CH:7]=[C:8]([N+:29]([O-:31])=[O:30])[CH:9]=3)[N:14]=[CH:13][C:12]=2[C:16]#[N:17])[CH:27]=[CH:26][CH:25]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 674DimethylamineHCID 11430Potassium CarbonateHCID 224666528-Bromomethyl-4-[(3-bromophenyl)-N-acetylamino]-6-nitro-3-quinolinecarbonitrile

Product 1

HCID 102026834-[(3-Bromophenyl)amino]-8-dimethylaminomethyl-6-nitro-3-quinolinecarbonitrile

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

To a stirred solution of dimethylamine in THF (2.0 M; 115 ml; 230 mmol) at 0° C. was added a solution of 8-bromomethyl 4[(3-bromophenyl)-N-acetylamino]- -6-nitro-3-quinolinecarbonitrile (11.6 g, 23 mmol) in 115 ml of THF during 15 m. After warming to 25° C. the mixture was stirred for 2 h. The THF was evaporated off, and the residue was refluxed in 230 ml of methanol with 12.7 g (92 mmol) of potassium carbonate for 1 h. The mixture was cooled, saturated with CO2, and concentrated. The residue was partitioned with methylene chloride and water. The organic layer was washed with water, dried, and concentrated. The residue was subjected to chromatography on silica gel with methylene chloride-ethyl acetate-methanol-triethylamine to give 6.0 g yellow solid, mp 223-226° C.

Workup

  1. customThe THF was evaporated off
  2. concentrationconcentrated
  3. customThe residue was partitioned with methylene chloride and water
  4. washThe organic layer was washed with water
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f78d64a18ffd4b858a37b0207c80f645
Source dataset
uspto-grants-1999_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06002008

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes