Acetic Acid → 6-Amino-4-[(3-bromophenyl)amino]-8-dimethylaminomethyl-3-quinolinecarbonitrile

HRID 548420Notes

Reaction equation

HRID 548420 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[C:14]([CH2:22][N:23]([CH3:25])[CH3:24])[CH:15]=[C:16]([N+:19]([O-])=O)[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:26]#[N:27])[CH:5]=[CH:6][CH:7]=1.C(O)(=O)C>[Fe].CO>[NH2:19][C:16]1[CH:17]=[C:18]2[C:13](=[C:14]([CH2:22][N:23]([CH3:24])[CH3:25])[CH:15]=1)[N:12]=[CH:11][C:10]([C:26]#[N:27])=[C:9]2[NH:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 102026834-[(3-Bromophenyl)amino]-8-dimethylaminomethyl-6-nitro-3-quinolinecarbonitrile

Product 1

HCID 101353526-Amino-4-[(3-bromophenyl)amino]-8-dimethylaminomethyl-3-quinolinecarbonitrileYield 59.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

A stirred mixture of 4-[(3-bromophenyl)amino]-8-dimethylaminomethyl-6-nitro-quinoline-3-carbonitrile (5.98 g, 14.1 mmol), iron powder (2.76 g, 49 mg-atoms), acetic acid (5.67 ml, 99 mmol), and 70 ml of methanol was refluxed for 2 h and then evaporated to remove methanol. The residue was stirred with water for 10 m, and the orange solid was filtered off and washed with 2% acetic acid. The total filtrate was basified to pH 10 with 5 N sodium hydroxide. The resulting precipitate was extracted with methylene chloride. The extract was washed with water, dried, and concentrated. The residue was subjected to chromatography on silica gel with ethyl acetate-methanol-triethylamine to give 3.34 g of amber solid; mass spectrum (electrospray, m/e) M+H 396.2, 398.1.

Workup

  1. temperaturewas refluxed for 2 h
  2. customevaporated
  3. customto remove methanol
  4. filtrationthe orange solid was filtered off
  5. washwashed with 2% acetic acid
  6. extractionThe resulting precipitate was extracted with methylene chloride
  7. washThe extract was washed with water
  8. customdried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-32e95f6b1bd84325b9f8c00b0ee9b315
Source dataset
uspto-grants-2011_05
Patent number
USRE042376E1

Reaction notes

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