Acetic Anhydride → HCID 18980357, compound

HRID 2392725Notes

Reaction equation

HRID 2392725 reaction equation
[NH2:1][C:2]1[C:3]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.[C:14](OC(=O)C)(=[O:16])[CH3:15]>O1CCOCC1>[C:14]([NH:1][C:2]1[C:3]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1)(=[O:16])[CH3:15]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 289723Ethyl 3-amino-5-chloropicolinate

Product 1

HCID 18980357HCID 18980357, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl 3-amino-5-chloropicolinate (107) (2.0 g, 10 mmol) in 10 mL of 1,4-dioxane was added 4 mL of acetic anhydride. The resulting solution was allowed to stir at 50° C. for 24 hr. Solvent was evaporated and water (10 mL) was added to the residue. The mixture was neutralized by saturated sodium bicarbonate solution to pH=7. A pale yellow solid was collected by filtration and dried in vacuo, giving 2.0 g (83%) of the product. mp 98°-100° C. 1H NMR (CDCl3): δ1.476 (t, J=7.2 Hz, 3H), 4.45 (q, J=7.2 Hz, 3H), 8.352 (d, J=2.1 Hz, 1H), 9.218 (d, J=2.1 Hz, 1H), 11.087 (s, 1H).

Workup

  1. customSolvent was evaporated
  2. additionwater (10 mL) was added to the residue
  3. filtrationA pale yellow solid was collected by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-ce0c1def00674e7fbaf855a00d02c544
Source dataset
uspto-grants-1998_09
Patent number
US05801183

Reaction notes

Loading…