Acetic Anhydride → 4-[(3-Bromophenyl)-N-acetylamino]-6,7-dihydroxy-3-quinolinecarbonitrile

HRID 612209Notes

Reaction equation

HRID 612209 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]([OH:20])=[C:16]([OH:19])[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:21]#[N:22])[CH:5]=[CH:6][CH:7]=1.CN(C1C=CC=CN=1)C.[C:32](OC(=O)C)(=[O:34])[CH3:33].C(=O)(O)[O-].[Na+]>O.CO.N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([N:8]([C:9]2[C:18]3[C:13](=[CH:14][C:15]([OH:20])=[C:16]([OH:19])[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:21]#[N:22])[C:32](=[O:34])[CH3:33])[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 7918Acetic AnhydrideHCID 218852-DimethylaminopyridineHCID 516892Sodium BicarbonateHCID 1354028484-(3-Bromophenylamino)-6,7-dihydroxy-3-quinolinecarbonitrile

Product 1

HCID 1356708254-[(3-Bromophenyl)-N-acetylamino]-6,7-dihydroxy-3-quinolinecarbonitrile

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A solution of 4-(3-bromophenylamino)-6,7-dihydroxy-3-quinolinecarbonitrile (1.78 g, 5.0 mmol), dimethylaminopyridine (60 mg, 0.50 mmol), 5.0 ml of acetic anhydride, and 10 ml of pyridine was stirred at reflux temperature for 1.5 h and concentrated to dryness. The residue was stirred with 50 ml of methanol, 5 ml of water, and sodium bicarbonate (2.1 g, 25 mmol) at 25° C. for 16 h and concentrated to dryness. The residue was stirred with water containing acetic acid to give pH-4-5, and the resulting solid was filtered off, washed with water, and dried. A solution of the resulting solid in THF was passed through a pad of silica gel; the filtrate was concentrated to give a tan solid; mass spectrum (electrospray, m/e) M-H 396.3, 398.3.

Workup

  1. temperatureat reflux temperature for 1.5 h
  2. concentrationconcentrated to dryness
  3. concentrationconcentrated to dryness
  4. additioncontaining acetic acid
  5. customto give pH-4-5
  6. filtrationthe resulting solid was filtered off
  7. washwashed with water
  8. customdried
  9. concentrationthe filtrate was concentrated
  10. customto give a tan solid

Sources & evidence

ORD record
ord-cefb0dda127c4aa08765ffe2d4fcc84b
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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