Potassium Hydroxide → 8-bromo-10H-chromeno[3,2-b]pyridin-10-one

HRID 1970290Notes

Reaction equation

HRID 1970290 reaction equation
[Br:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[C:8]([C:13]#N)=[N:9][CH:10]=[CH:11][CH:12]=2)=[CH:4][CH:3]=1.[OH-:17].[K+]>>[Br:1][C:2]1[CH:16]=[CH:15][C:5]2[O:6][C:7]3[C:8](=[N:9][CH:10]=[CH:11][CH:12]=3)[C:13](=[O:17])[C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 14797Potassium HydroxideHCID 667281343-(4-Bromophenoxy)picolinonitrile

Product 1

HCID 584662358-bromo-10H-chromeno[3,2-b]pyridin-10-one

Conditions

Temperature
190 °C

Procedure

A mixture of 3-(4-bromophenoxy)picolinonitrile (57 g, 207 mmol) and 300 g of PPA was stirred at 190° C. for 2 h, followed by 180° C. overnight. After cooling to RT, the reaction mixture was poured into 500 g of ice water. After the PH was adjusted to 7 with KOH, the suspension was filtered. The solid was washed with large excess of water, followed by washing with methanol and acetone. The resulting solid was air dried to give 8-bromo-10H-chromeno[3,2-b]pyridin-10-one as a tan solid with >90% purity. The material was carried on to the next step.

Workup

  1. waitfollowed by 180° C. overnight
  2. temperatureAfter cooling to RT
  3. filtrationthe suspension was filtered
  4. washThe solid was washed with large excess of water
  5. washby washing with methanol and acetone
  6. customdried

Sources & evidence

ORD record
ord-89032c71b17340ba9c7e9e855eed0182
Source dataset
uspto-grants-2013_04
Patent number
US08426447B2

Reaction notes

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