Water → 2-Oxo-2,3-dihydro-1,3-benzoxazole-6-carbaldehyde

HRID 590380Notes

Reaction equation

HRID 590380 reaction equation
[O:1]=[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]#N)=[CH:10][C:4]=2[O:3]1.[OH2:13]>C(O)=O.[Al].[Ni]>[O:1]=[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([CH:11]=[O:13])=[CH:10][C:4]=2[O:3]1

Participants

5

Reactant 2

HCID 962WaterHCID 101762552-Oxo-2,3-dihydro-1,3-benzoxazole-6-carbonitrile2×

Product 1

HCID 3914742-Oxo-2,3-dihydro-1,3-benzoxazole-6-carbaldehydeYield 97%

Reagents, catalysts & solvents 2

HCID 6336846Nickel aluminideCatalystHCID 284Formic AcidSolvent

Procedure

A mixture of 2-oxo-2,3-dihydro-1,3-benzoxazole-6-carbonitrile (Intermediate 6, 220 mg; 1.37 mmol) and aluminium/nickel 1:1 alloy (223.6 mg; 2.61 mmol) in 2.25 ml of formic acid and 0.75 ml of water is stirred at 90° C. for 24 hr. The solid is filtered and washed with ethanol. The filtrate is concentrated in vacuo and dried overnight at 45° C. in a vacuum dessicator. The solid obtained (219 mg; 97% yield) is pure enough as to prosecute with the synthesis.

Workup

  1. filtrationThe solid is filtered
  2. washwashed with ethanol
  3. concentrationThe filtrate is concentrated in vacuo
  4. customdried overnight at 45° C. in a vacuum dessicator
  5. customThe solid obtained (219 mg; 97% yield)
  6. customto prosecute with the synthesis

Sources & evidence

ORD record
ord-04d1fd0ab62f4ec8b9f59e80b98d7d2c
Source dataset
uspto-grants-2016_01
Patent number
US09233108B2

Reaction notes

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