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

HRID 1378425Notes

Reaction equation

HRID 1378425 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 (1.1 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-8ab651f12cd948689fb4c9eebbe55100
Source dataset
uspto-grants-1997_09
Patent number
US05668154

Reaction notes

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