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

HRID 1768922Notes

Reaction equation

HRID 1768922 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>[Br:21][C:8]1[N:7]=[CH:6][CH:5]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[C:3]=1[C:17]([O:19][CH3:20])=[O:18]

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

To a solution of 80.0 g (0.28 mol) of 1-cyano-1-methoxycarbonyl-4-(N,N-dimethylamino)-2-(4-chlorophenyl)-1,3-butadiene in 100 ml of acetic acid, an acetic acid solution of 25% HBr was then gradually added dropwise at room temperature with 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 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. customdried

Sources & evidence

ORD record
ord-9f8a1052f1ec47aeb20ed0c9064c34c4
Source dataset
uspto-grants-1995_01
Patent number
US05380700

Reaction notes

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