Hydrazine hydrate (1:1) → 2-Methyl-5-benzoxazolemethanamine

HRID 594380Notes

Reaction equation

HRID 594380 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([CH2:11][N:12]3C(=O)C4C(=CC=CC=4)C3=O)=[CH:7][C:5]=2[N:6]=1.O.NN>CCO>[CH3:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([CH2:11][NH2:12])=[CH:7][C:5]=2[N:6]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86695629HCID 86695629, compound

Product 1

HCID 532566422-Methyl-5-benzoxazolemethanamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-((2-methylbenzo[d]oxazol-5-yl)methyl)isoindoline-1,3-dione (200 mg; 0.68 mmol), and hydrazine monohydrate (715 mg; 21.89 mmol) in EtOH (30 ml) was refluxed, under nitrogen, for 4 h. After cooling to rt, the mixture was filtered, and the filtrate was concentrated to dryness under reduced pressure affording (2-methylbenzo[d]oxazol-5-yl)methanamine as an orange oil. LC-MS (conditions D): tR=0.50 min.; [M+H]+: 163.07 g/mol.

Workup

  1. temperaturewas refluxed, under nitrogen, for 4 h
  2. filtrationthe mixture was filtered
  3. concentrationthe filtrate was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-9e98c9baa584492d89331db619fea72d
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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