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

HRID 548409Notes

Reaction equation

HRID 548409 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-d47ddc9600ac4c12b340b1c6632d45ac
Source dataset
uspto-grants-2011_05
Patent number
USRE042376E1

Reaction notes

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