Formic Acid → HCID 86681100, compound

HRID 1848127Notes

Reaction equation

HRID 1848127 reaction equation
C(OC(=O)C)(=O)C.[CH:8]([OH:10])=O.[Br:11][C:12]1[CH:13]=[C:14]([N+:21]([O-:23])=[O:22])[C:15]([NH2:20])=[N:16][C:17]=1[O:18][CH3:19]>>[Br:11][C:12]1[CH:13]=[C:14]([N+:21]([O-:23])=[O:22])[C:15]([NH:20][CH:8]=[O:10])=[N:16][C:17]=1[O:18][CH3:19]

Participants

4

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 534081225-Bromo-6-methoxy-3-nitropyridin-2-amine

Product 1

HCID 86681100HCID 86681100, compoundYield 94.9%

Conditions

Temperature
60 °C

Procedure

A mixture of acetic anhydride (15.9 mL, 168.7 mmol) and formic acid (6.4 mL, 168.7 mmol) was heated at 60° C. for 3 h. After cooling to rt, 5-bromo-6-methoxy-3-nitropyridin-2-amine (2.1 g, 8.4 mmol) from Step 1 of this Example was added in portions. The resulting mixture was heated at 60° C. for 1 h, then at 70° C. for 1 h. LCMS analysis showed that the reaction was complete. The volume was condensed under reduced pressure, and the precipitated solid was collected by filtration to give N-(5-bromo-6-methoxy-3-nitropyridin-2-yl)formamide as a light yellow solid (2.2 g, 94%). LCMS (ESI) m/z 276, 278 (M+H)+.

Workup

  1. temperatureAfter cooling to rt
  2. temperatureThe resulting mixture was heated at 60° C. for 1 h
  3. customcondensed under reduced pressure
  4. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-3526b7931c2e4fba80c4469ea52bcdf0
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

Loading…