Methyl bromoacetate → [4-(3-Benzo[d]isoxazolylimino)-1-(4H)-pyridinyl]-acetic acid methyl ester hydrobromide

HRID 617202

Reaction equation

HRID 617202 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[O:10][N:9]=2)=[CH:3][CH:2]=1.[Br:17][CH2:18][C:19]([O:21][CH3:22])=[O:20]>C(#N)C>[BrH:17].[CH3:22][O:21][C:19](=[O:20])[CH2:18][N:1]1[CH:2]=[CH:3][C:4](=[N:7][C:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[O:10][N:9]=2)[CH:5]=[CH:6]1

Participants

4

Reactant 2

HCID 60984Methyl bromoacetateHCID 98372191,2-Benzisoxazol-3-amine, N-4-pyridinyl-

Product 1

HCID 70280625[4-(3-Benzo[d]isoxazolylimino)-1-(4H)-pyridinyl]-acetic acid methyl ester hydrobromideYield 70%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-(4-pyridinylamino)-1,2-benzisoxazole (0.9g, 4.3 mmol) and methyl bromoacetate (0.44 mL, 1. 1 eq) in acetonitrile (25 mL) was heated at reflux for one hour. The mixture was then allowed to cool to room temperature and the precipitated product was collected by filtration. The white solid was washed with diethyl ether and dried under vacuum to provide the title compound (1 g, 70%), mp 235-236° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for one hour
  3. filtrationthe precipitated product was collected by filtration
  4. washThe white solid was washed with diethyl ether
  5. customdried under vacuum

Sources & evidence

ORD record
ord-899c2dfdacb74f298f0d913a6f0755a0
Source dataset
uspto-grants-1999_09
Patent number
US05948798

Linked notes

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