Bromine → 2-Amino-5-bromopyridine-3-carboxylic acid--hydrogen bromide (1/1)

HRID 1362100Notes

Reaction equation

HRID 1362100 reaction equation
[Br:1]Br.[NH2:3][C:4]1[N:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]>C(O)(=O)C>[BrH:1].[NH2:3][C:4]1[N:12]=[CH:11][C:10]([Br:1])=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 24408Bromine2×HCID 729302-Aminonicotinic acid

Product 1

HCID 573505542-Amino-5-bromopyridine-3-carboxylic acid--hydrogen bromide (1/1)Yield 183.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bromine (7.5 mL, 146 mmol) was added dropwise over 10 min to a suspension of 2-amino-nicotinic acid (20.0 g, 145 mmol) in glacial acetic acid (250 mL) cooled in an ice bath. After the bromine addition was complete, the mixture was stirred at ambient temperature for 2 d. The resulting light yellow solid was isolated by filtration, washed with Et2O, and dried under high vacuum (40° C.) for several hours to give the title compound (40.0 g, 93%): 1H NMR (300 MHz, DMSO-d6) δ 8.33 (d, J=2.5 Hz, 1H), 8.20 (d, J=2.5 Hz, 1H), 8.02 (bs, 3H); ESI MS m/e 217 (M+H)+.

Workup

  1. temperaturecooled in an ice bath
  2. customThe resulting light yellow solid was isolated by filtration
  3. washwashed with Et2O
  4. customdried under high vacuum (40° C.) for several hours

Sources & evidence

ORD record
ord-1a2c058611d147c59d84997afa6c5b1f
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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