Sulfuric Acid → 3-Amino-6-bromo-N-methoxypyridine-2-carboxamide

HRID 2279834Notes

Reaction equation

HRID 2279834 reaction equation
[NH2:1][C:2]1[C:3]([C:8]([NH:10][O:11][CH3:12])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.S(=O)(=O)(O)O.[Br:18]Br>O.CC(O)=O>[NH2:1][C:2]1[C:3]([C:8]([NH:10][O:11][CH3:12])=[O:9])=[N:4][C:5]([Br:18])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 24408BromineHCID 866977753-amino-N-methoxypyridine-2-carboxamide2×

Product 1

HCID 866977743-Amino-6-bromo-N-methoxypyridine-2-carboxamideYield 59.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

A suspension of 3-amino-N-methoxypyridine-2-carboxamide (Compound 46E, 0.275 g, 1.64 mmol) in H2O (4.5 mL) was treated with a drop of Sulfuric acid and 0.6 mL of AcOH. After about 10 min of vigorous stirring, a solution of Bromine (84.7 uL, 1.64 mmol) in 0.4 mL of AcOH was cautiously added. After an additional 15-20 min of stirring the texture of the reaction mixture/suspension changed to become a more coarse orange ppt. This material was collected by filtration and dried to afford 240 mg of the title compound as an orange solid (59%). 1H NMR (400 MHz, DMSO-d6) δ 11.51 (s, 1H), 7.40 (d, J=8.8 Hz, 1H), 7.14 (d, J=8.8 Hz, 1H), 6.91 (br. s., 2H), 3.66 (s, 3H); MS (ESI): m/z=245.98, 247.98 [M+H]+; UPLC: tR=0.67 min (UPLC-TOF: polar—2 min)

Workup

  1. filtrationThis material was collected by filtration
  2. customdried

Sources & evidence

ORD record
ord-b80886e9805845d385209279e7c892fa
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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