Acetic Acid → 4-Amino-7-cyano-2-methylbenzoxazole

HRID 751058Notes

Reaction equation

HRID 751058 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[C:10]([C:11]#[N:12])=[CH:9][CH:8]=[C:7]([N+:13]([O-])=O)[C:5]=2[N:6]=1.CC(O)=O>CCOC(C)=O.[Fe]>[NH2:13][C:7]1[C:5]2[N:6]=[C:2]([CH3:1])[O:3][C:4]=2[C:10]([C:11]#[N:12])=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 218752867-Cyano-2-methyl-4-nitrobenzoxazole

Product 1

HCID 218749104-Amino-7-cyano-2-methylbenzoxazoleYield 102.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 11B (0.16 g, 0.79 mmol) in EtOAc (2 mL) was added iron powder (0.1 g), followed by 10% aqueous AcOH (2 mL). The mixture was stirred at 60° C. for 2 h, then allowed to cool to rt and partitioned between saturated NaHCO3 and EtOAc. The separated EtOAc layer was concentrated under reduced pressure to give the title compound (0.14 g) as a solid.

Workup

  1. temperatureto cool to rt
  2. custompartitioned between saturated NaHCO3 and EtOAc
  3. concentrationThe separated EtOAc layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9c01aa225de8405289c2ad886cce5678
Source dataset
uspto-grants-2008_07
Patent number
US07405234B2

Reaction notes

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