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

HRID 1970292Notes

Reaction equation

HRID 1970292 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 stirred 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-b1d76feed5994374a7a9f9e3c5ce8613
Source dataset
uspto-grants-2013_04
Patent number
US08426447B2

Reaction notes

Loading…