Hydrogen Bromide → HCID 20481484, compound

HRID 1649015Notes

Reaction equation

HRID 1649015 reaction equation
[N:1]1[C:2]([C:10]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]3[C:11]=2[CH:12]=[CH:13][C:14](=[O:22])[NH:15]3)=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[Br:23]Br.[BrH:25]>C(O)(=O)C.CC(C)=O>[OH2:20].[BrH:23].[Br:25][C:3]1[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]2=[N:1][C:2]=1[C:10]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]2[C:11]=1[CH:12]=[CH:13][C:14](=[O:22])[NH:15]2

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 24408BromineHCID 13260243HCID 13260243, compound

Product 1

HCID 20481484HCID 20481484, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 180AcetoneSolvent

Procedure

To a solution of 5-(imidazo[1,2-a]pyridine-2-yl)-8-methoxycarbostyril (4 g) in acetic acid (80 ml) was added dropwise at room temperature a solution of bromine (2.22 g) in acetic acid (5 ml). After completion of addition, the mixture was stirred for 3 hours. Crystals which precipitated were collected by filtration and washed with diethyl ether. The crystals thus obtained were dissolved in acetone and the solution was adjusted to pH of about 1 by the addition of 48% hydrobromic acid. Crystals which precipitated were collected by filtration and recrystallized from methanol-water to give 5 g of 5-(3-bromoimidazo[1,2-a]pyridine-2-yl)-8-methoxycarbostyril monohydrobromide monohydrate.

Workup

  1. additionAfter completion of addition
  2. customCrystals which precipitated
  3. filtrationwere collected by filtration
  4. washwashed with diethyl ether
  5. customThe crystals thus obtained
  6. customCrystals which precipitated
  7. filtrationwere collected by filtration
  8. customrecrystallized from methanol-water

Sources & evidence

ORD record
ord-5a2c43dd5317492d85f35913840e27d6
Source dataset
uspto-grants-1983_11
Patent number
US04414390

Reaction notes

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