Water → 8-Bromo-2,3-dihydro-2-phenylbenzofuro[3,2-b]pyridin-4(1H)-one

HRID 869380Notes

Reaction equation

HRID 869380 reaction equation
[C:1]([C:11]1[O:12][C:13]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][C:14]=2[C:15]=1[NH2:16])(=[O:10])/[CH:2]=[CH:3]\[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O>CC(O)=O.OP(O)(O)=O>[Br:21][C:18]1[CH:19]=[CH:20][C:13]2[O:12][C:11]3[C:1](=[O:10])[CH2:2][CH:3]([C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=4)[NH:16][C:15]=3[C:14]=2[CH:17]=1

Participants

5

Reactant 2

HCID 962WaterHCID 86722227HCID 86722227, compound

Product 1

HCID 867222268-Bromo-2,3-dihydro-2-phenylbenzofuro[3,2-b]pyridin-4(1H)-oneYield 85%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1004Phosphoric AcidSolvent

Procedure

A solution of (Z)-2-cinnamoyl-3-amino-5-bromo-benzofuran (28 g, 81.83 mmol) in AcOH (70 mL) and H3PO4 (70 mL) was refluxed for 2 hours. TLC showed the reaction completed. The mixture was cooled to room temperature and poured into water (250 mL) The yellow solids precipitated out were collected by filtration to give 8-bromo-2-phenyl-2,3-dihydro-benzofuro[3,2-b]pyridin-4(1H)-one (6C) (23.8 g, 85% yield).

Workup

  1. customprecipitated out
  2. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-57ae42fdbf5f4e9d9815981be478f1b8
Source dataset
uspto-grants-2015_03
Patent number
US08969373B2

Reaction notes

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