Methanol → 6-Amino-4-[(3-bromophenyl)amino]-7-methoxy-quinoline-3-carbonitrile

HRID 379106Notes

Reaction equation

HRID 379106 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:22][CH3:23])=[C:16]([N+:19]([O-])=O)[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:24]#[N:25])[CH:5]=[CH:6][CH:7]=1.[Cl-].[NH4+].CO>O.C(OCC)(=O)C.[Fe]>[NH2:19][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][C:15]=1[O:22][CH3:23])[N:12]=[CH:11][C:10]([C:24]#[N:25])=[C:9]2[NH:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1

Participants

7

Reactant 3

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 98438404-[(3-Bromophenyl)amino]-7-methoxy-6-nitro-quinoline-3-carbonitrile

Product 1

HCID 98206456-Amino-4-[(3-bromophenyl)amino]-7-methoxy-quinoline-3-carbonitrileYield 69%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2.05 g (5.1 mmol) of 4-[(3-bromophenyl)amino]-7-methoxy-6-nitro-quinoline-3-carbonitrile, 1.37 g (25.7 mmol) of ammonium chloride, and 0.86 g (15.4 mmol) of powdered iron was stirred at reflux in 26 ml water and 26 ml methanol for 2 hours. The mixture was diluted with ethyl acetate and the hot mixture was filtered. The organic layer was separated from the filtrate and dried over magnesium sulfate. The solvent was removed and the residue was chromatographed on silica gel eluting with mixtures of chloroform and ethyl acetate. Product fractions were combined to give 1.3 g of 6-amino-4-[(3-bromophenyl)amino]-7-methoxy-quinoline-3-carbonitrile as a yellow solid: mass spectrum (electrospray, m/e): M+H 369.1, 371.1.

Workup

  1. filtrationthe hot mixture was filtered
  2. customThe organic layer was separated from the filtrate
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed
  5. customthe residue was chromatographed on silica gel eluting with mixtures of chloroform and ethyl acetate

Sources & evidence

ORD record
ord-8c49d0103cef4e999a69564456d10362
Source dataset
uspto-grants-2001_10
Patent number
US06297258B1

Reaction notes

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