2-Amino-5-bromopyridine → HCID 54716333, compound

HRID 2232106Notes

Reaction equation

HRID 2232106 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[OH:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:12][C:11]=1[C:26](OCC)=[O:27]>C1(C)C=CC=CC=1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:26]([C:11]2[CH2:12][N:13]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:14]3[C:19]([C:10]=2[OH:9])=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:27])=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 706222-Amino-5-bromopyridineHCID 85585358HCID 85585358, compound

Product 1

HCID 54716333HCID 54716333, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 21.98 g of 2-amino-5-bromopyridine and 25.0 g of 1,2-dihydro-4-hydroxy-1-phenyl-3-quinolinecarboxylic acid, ethyl ester in 250 ml of toluene was refluxed for 24 hours in a soxhlet apparatus containing 20 g of 4 Å molecular sieves. Evaporation of the volatiles afforded a residue which was purified by means of high pressure liquid chromatography (silica gel: dichloromethane as the eluent). The resultant solution was degassed and evaporated to yield 23.56 g (66%) of N-(5-bromo-2-pyridyl)-1,2-dihydro-4-hydroxy-1-phenyl-3-quinolinecarboxamide, m.p. 153°-154° C.

Workup

  1. additioncontaining 20 g of 4 Å molecular sieves
  2. customEvaporation of the volatiles
  3. customafforded a residue which
  4. customwas purified by means of high pressure liquid chromatography (silica gel
  5. customThe resultant solution was degassed
  6. customevaporated

Sources & evidence

ORD record
ord-10612abb78df4af8a6949fb8f6b898ee
Source dataset
uspto-grants-1988_11
Patent number
US04786644

Reaction notes

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