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

HRID 1108247Notes

Reaction equation

HRID 1108247 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Br:11]Br>C(O)(=O)C.C(OCC)C>[BrH:11].[NH2:1][C:2]1[C:3]([C:4]([OH:6])=[O:5])=[CH:7][C:8]([Br:11])=[CH:9][N:10]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 729302-Aminonicotinic acid

Product 1

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

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 3.6 g 2-amino-nicotinic acid in 450 mL of glacial acetic acid was treated with a solution of 4 mL of bromine in 50 mL of glacial acetic acid over 10-15 min. The resulting mixture was stirred at room temperature for 2 h, diluted with 2 L of diethyl ether, and the ensuing precipitate was filtered and dried to provide 6.1 g of the title compound of Step A as a solid melting at 280° C. (decompose) (lit1. m.p. 280° C., decomposed). 1H NMR (400 MHz, Me2SO-d6): δ 7.38 (br s,2H), 8.08 (s,1H), 8.25 (s,1H), 13.45 (br s,1H). (1U.S. Pat. No. 3,950,160)

Workup

  1. filtrationthe ensuing precipitate was filtered
  2. customdried

Sources & evidence

ORD record
ord-7333e5c24b5d4f06918d5b90912db43d
Source dataset
uspto-grants-2000_05
Patent number
US06066638

Reaction notes

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