Hydrogen Bromide → 2-Bromo-4-(4-chloro-phenyl)-nicotinic acid methyl ester

HRID 1770083Notes

Reaction equation

HRID 1770083 reaction equation
C([C:3]([C:17]([O:19][CH3:20])=[O:18])=[C:4]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)[CH:5]=[CH:6][N:7](C)[CH3:8])#N.[BrH:21]>C(O)(=O)C>[CH3:20][O:19][C:17](=[O:18])[C:3]1[C:4]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[CH:5][CH:6]=[N:7][C:8]=1[Br:21]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 53771739HCID 53771739, compound

Product 1

HCID 200952582-Bromo-4-(4-chloro-phenyl)-nicotinic acid methyl esterYield 83.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

80.0 g (0.28 mol) of 1-cyano-1-methoxycarbonyl-4-(N,N-dimethylamino)-2-(4-chlorophenyl)-1,3-butadiene was weighed, and 100 ml of acetic acid was added thereto and an acetic acid solution of 25% HBr was then gradually added dropwise thereto at room temperature under stirring. After the dropwise addition, the resultant mixture was stirred at room temperature for 3 hours. The reaction mixture was then poured into ice water to precipitate a crystal. The crystal thus precipitated was filtrated out and washed with water and was dried to obtain 75.0 g of a white crystal of the aimed product.

Workup

  1. additionAfter the dropwise addition
  2. customto precipitate a crystal
  3. customThe crystal thus precipitated
  4. filtrationwas filtrated out
  5. washwashed with water
  6. customwas dried

Sources & evidence

ORD record
ord-6481f8725d494fe6b97ec1e2353aa0e3
Source dataset
uspto-grants-1995_01
Patent number
US05385880

Reaction notes

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