Acetic Anhydride → N-(6-bromo-2-methoxypyridin-3-yl)formamide

HRID 1477758Notes

Reaction equation

HRID 1477758 reaction equation
[C:1](OC(=O)C)(=[O:3])C.[Br:8][C:9]1[N:14]=[C:13]([O:15][CH3:16])[C:12]([NH2:17])=[CH:11][CH:10]=1>C(O)=O>[Br:8][C:9]1[N:14]=[C:13]([O:15][CH3:16])[C:12]([NH:17][CH:1]=[O:3])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 105361376-Bromo-2-methoxypyridin-3-amine

Product 1

HCID 71492501N-(6-bromo-2-methoxypyridin-3-yl)formamide

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Acetic anhydride (203 mL) was added dropwise to formic acid (204 mL) under ice-cooling, and the mixture was stirred at the same temperature for 25 min. 6-bromo-2-methoxypyridine-3-amine power (CAS#89466-18-2, 146 g) was put into the reaction mixture over 10 minutes, and the reaction solution was stirred at the same temperature for 30 minutes. The water bath was removed. tert-Butyl methyl ether (300 mL) and n-heptane (500 mL) were sequentially added dropwise to the reaction solution, and then the reaction solution was stirred for 30 minutes.

Workup

  1. temperaturecooling
  2. stirringthe reaction solution was stirred at the same temperature for 30 minutes
  3. customThe water bath was removed
  4. additiontert-Butyl methyl ether (300 mL) and n-heptane (500 mL) were sequentially added dropwise to the reaction solution
  5. stirringthe reaction solution was stirred for 30 minutes

Sources & evidence

ORD record
ord-7dbc1321592c4118ac8de29ccdc1af20
Source dataset
uspto-grants-2016_08
Patent number
US09403815B2

Reaction notes

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