7-Cyano-2-methyl-4-nitrobenzoxazole → 4-Amino-7-cyano-2-methylbenzoxazole

HRID 966925Notes

Reaction equation

HRID 966925 reaction equation
[C:1]([C:3]1[C:11]2[O:10][C:9]([CH3:12])=[N:8][C:7]=2[C:6]([N+:13]([O-])=O)=[CH:5][CH:4]=1)#[N:2]>CCOC(C)=O.[Fe]>[NH2:13][C:6]1[C:7]2[N:8]=[C:9]([CH3:12])[O:10][C:11]=2[C:3]([C:1]#[N:2])=[CH:4][CH:5]=1

Participants

4

Reactant 1

HCID 218752867-Cyano-2-methyl-4-nitrobenzoxazole

Product 1

HCID 218749104-Amino-7-cyano-2-methylbenzoxazoleYield 89%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

Compound 477C (0.156 g, 0.77 mmol) was dissolved in a 1:1 mixture of EtOAc/10% HOAc (20 mL) and heated to 65° C. Iron powder (325 mesh, 0.214 g, 3.83 mmol) was added and the reaction was stirred for 4 h. The cooled mixture was filtered through Celite and the resulting filtrate was washed with water (25 mL), brine (25 mL), dried over MgSO4, and concentrated to give compound 477D (0.118 g, 89%) as an orange solid. HPLC: 87% at 2.03 min (retention time) (YMC S5 ODS column, 4.6×50 mm, eluting with 10-90% aqueous methanol over 4 min containing 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm). MS (ES): m/z 174.05 [M+H]+.

Workup

  1. filtrationThe cooled mixture was filtered through Celite
  2. washthe resulting filtrate was washed with water (25 mL), brine (25 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4033e98ff4684e29bab3268bf396812e
Source dataset
uspto-grants-2005_10
Patent number
US06953679B2

Reaction notes

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