Hydrazine hydrate (1:1) → 2-(Aminomethyl)-N-[2-(3-chlorophenyl)ethyl]-4-oxazolecarboxamide

HRID 1009199Notes

Reaction equation

HRID 1009199 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][NH:10][C:11]([C:13]2[N:14]=[C:15]([CH2:18][N:19]3C(=O)C4C(=CC=CC=4)C3=O)[O:16][CH:17]=2)=[O:12])[CH:5]=[CH:6][CH:7]=1.O.NN>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][NH:10][C:11]([C:13]2[N:14]=[C:15]([CH2:18][NH2:19])[O:16][CH:17]=2)=[O:12])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 57787040HCID 57787040, compound

Product 1

HCID 577870212-(Aminomethyl)-N-[2-(3-chlorophenyl)ethyl]-4-oxazolecarboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-oxazole-4-carboxylic acid [2-(3-chloro-phenyl)-ethyl]-amide (0.75 g, 1.8 mmol) was dissolved in ethanol (5 mL). Hydrazine monohydrate (0.44 mL, 9.2 mmol) was added. The mixture was stirred for 12 hours. A white precipitate formed during the course of the reaction. The mixture was filtered and the solid was washed with methanol. The filtrate was reduced in vacuo to afford the title compound: 1H NMR (400 MHz, d6-DMSO): 8.46 (s, 1H), 8.27 (t, 1H), 7.27 (m, 3H), 7.16 (m, 1H), 3.78 (s, 2H), 3.45 (m, 2H), 2.82 (t, 2H); MS (ESI-LCMS) for C13H14ClN3O2: 280 (MH+).

Workup

  1. customA white precipitate formed during the course of the reaction
  2. filtrationThe mixture was filtered
  3. washthe solid was washed with methanol

Sources & evidence

ORD record
ord-80300b853222451f9d95da7ef2ff5211
Source dataset
uspto-grants-2011_07
Patent number
US07973061B2

Reaction notes

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