Acetic Anhydride → HCID 13773036, compound

HRID 980197Notes

Reaction equation

HRID 980197 reaction equation
[NH2:1][C:2]1[C:3]([F:15])=[C:4]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[C:5]([F:8])=[CH:6][CH:7]=1.[C:16](OC(=O)C)(=[O:18])[CH3:17]>C(O)C>[C:16]([NH:1][C:2]1[C:3]([F:15])=[C:4]([C:9]2[CH:10]=[CH:11][N:12]=[CH:13][CH:14]=2)[C:5]([F:8])=[CH:6][CH:7]=1)(=[O:18])[CH3:17]

Participants

4

Reactant 2

HCID 7918Acetic Anhydride2×HCID 13773037HCID 13773037, compound

Product 1

HCID 13773036HCID 13773036, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-(3-amino-2,6-difluorophenyl)-pyridine (6.5 g), acetic anhydride (4.9 g) and ethanol (200 ml) was heated at reflux. After 1 hour, a further 3.3 ml acetic anhydride was added and a third portion (1.5 ml) after another 3.5 hours. Reflux was continued for a total of 6 hours after which time the solution was cooled and evaporated and the residue was partitioned between aqueous sodium bicarbonate and chloroform. The organic layer was washed with water, dried and evaporated to give the solid product of m.p. 148°-150° C. (6.8 g, 86% yield). NMR (CDCl3, 60 MHz): 8.8 (m, 2H), 8.05 (m, 2H), 7.4 (m, 2H), 6.9 (m, 1H), 2.2 (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. waita third portion (1.5 ml) after another 3.5 hours
  4. temperatureReflux
  5. customwas continued for a total of 6 hours
  6. temperaturewas cooled
  7. customevaporated
  8. customthe residue was partitioned between aqueous sodium bicarbonate and chloroform
  9. washThe organic layer was washed with water
  10. customdried
  11. customevaporated
  12. customto give the solid product of m.p. 148°-150° C. (6.8 g, 86% yield)

Sources & evidence

ORD record
ord-4f9bfcc1ba38465ea11cb9e619086b06
Source dataset
uspto-grants-1987_01
Patent number
US04636506

Reaction notes

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