Water → 3-(formylamino)-6-bromo-3,4-dihydro-2(1H)quinolinone

HRID 1648307Notes

Reaction equation

HRID 1648307 reaction equation
[Br:1]Br.[CH:3]([NH:5][CH:6]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][C:7]1=[O:16])=[O:4].C([O-])(=O)C.[Na+].O>C(O)(=O)C>[CH:3]([NH:5][CH:6]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([Br:1])[CH:13]=2)[NH:8][C:7]1=[O:16])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 24408BromineHCID 517045Sodium AcetateHCID 179327143-(Formylamino)-3,4-dihydro-2(1H)quinolinone

Product 1

HCID 199194713-(formylamino)-6-bromo-3,4-dihydro-2(1H)quinolinoneYield 66.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bromine (16.0 g, 0.1 mol) was added to a stirred solution of 3-(formylamino)-3,4-dihydro-2(1H)quinolinone (19.0 g, 0.1 tool) and anhydrous sodium acetate (12.7 g, 0.2 tool) in acetic acid (500 mL). After 1 hour, water (1.5 L) was added and the precipitate was filtered off and air dried to give 17.8 g of 3-(formylamino)-6-bromo-3,4-dihydro-2(1H)quinolinone, mp 275°-282° C. This was dissolved in trifluoracetic acid (300 mL) and sodium nitrate (9.0 g) was added to the stirred solution. After I hour, water was added and the precipitate was filtered off and air dried to give 18.2 g of 3-(formylamino)-6-bromo-3,4-dihydro-8-nitro-2(1H) quinolinone, mp 232°-235° C.

Workup

  1. filtrationthe precipitate was filtered off
  2. customair dried

Sources & evidence

ORD record
ord-34d82283ed9240598623151a87012060
Source dataset
uspto-grants-1995_07
Patent number
US05436240

Reaction notes

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