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

HRID 406318Notes

Reaction equation

HRID 406318 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 minutes. 6-Bromo-2-methoxypyridine-3-amine powder (CAS #89466-18-2, 146 g) was put into the reaction mixture over 10 minutes, and then 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. The precipitated powder was collected by filtration. The resulting powder was crushed with a mortar, washed with tert-butyl methyl ether and then dried under reduced pressure to obtain 137.4 g of the title compound.

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
  6. filtrationThe precipitated powder was collected by filtration
  7. customThe resulting powder was crushed with a mortar
  8. washwashed with tert-butyl methyl ether
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-885ca24e062e4198b06b71a83abe583a
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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