Dimethylformamide → 8-bromo-2-chloro-10H-chromeno[3,2-b]pyridin-10-one

HRID 529419Notes

Reaction equation

HRID 529419 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[N+:7]([O-])[CH:8]=[CH:9][CH:10]=3)[C:5](=[O:17])[C:4]=2[CH:3]=1.P(Cl)(Cl)([Cl:20])=O.CN(C=O)C>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[N:7][C:8]([Cl:20])=[CH:9][CH:10]=3)[C:5](=[O:17])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 667282008-bromo-10-oxo-10H-chromeno[3,2-b]pyridine 1-oxide

Product 1

HCID 584661968-bromo-2-chloro-10H-chromeno[3,2-b]pyridin-10-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 8-bromo-10-oxo-10H-chromeno[3,2-b]pyridine 1-oxide in 100 mL of toluene at 0° C. was added dropwise phosphorus oxychloride (35.8 mL, 391 mmol) followed by 2 mL of DMF and the mixture was stiffed at RT overnight. The solvent was evaporated under vacuum and the residue which crashed out of water, was filtered and washed with water, methanol and acetone in sequence. The solid was air dried to give 8-bromo-2-chloro-10H-chromeno[3,2-b]pyridin-10-one as a tan solid.

Workup

  1. customThe solvent was evaporated under vacuum
  2. filtrationwas filtered
  3. washwashed with water, methanol and acetone in sequence
  4. customdried

Sources & evidence

ORD record
ord-37add0afa81a470c9c8135b2d4b116be
Source dataset
uspto-grants-2016_05
Patent number
US09346827B2

Reaction notes

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