Acetic Anhydride → HCID 13773036, compound

HRID 2291672Notes

Reaction equation

HRID 2291672 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 (CDC13, 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-75ccd2cffc434a16bafb367d4d9a6b7a
Source dataset
uspto-grants-1989_01
Patent number
US04797490

Reaction notes

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