2-Methyl-6-nitrobenzoxazole → 2-Methyl-1,3-benzoxazol-6-amine

HRID 1428921Notes

Reaction equation

HRID 1428921 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[CH:10]=[C:9]([N+:11]([O-])=O)[CH:8]=[CH:7][C:5]=2[N:6]=1>CO.[Pd]>[CH3:1][C:2]1[O:3][C:4]2[CH:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

4

Reactant 1

HCID 797662-Methyl-6-nitrobenzoxazole

Product 1

HCID 5905392-Methyl-1,3-benzoxazol-6-amineYield 101.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-Methyl-6-nitrobenzoxazole (10.0 g, 56 mmol) and 10% Pd/C (3.4 g) in MeOH (10 mL) were hydrogenated at rt for 16 h. The reaction mixture was filtered through Celite and wash with MeOH (100 mL). The filtrate was concentrated under vacuum to obtained crude 2-methylbenzo[d]oxazol-6-amine (8.4 g), (MS: ESI +ve, 149.07 [M+H]); 1H NMR: (400 MHz, DMSO) δ: 2.47 (s, 3H), 5.24 (s, 2H), 6.56-6.53 (dd, J=2, 1H), 6.70-6.70 (d, J=1.6, 1H), 7.25-7.23 (d, J=8.4, 1H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. washwash with MeOH (100 mL)
  3. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-9a643945eb304ce0a5a41b5c2a740d0c
Source dataset
uspto-grants-2015_01
Patent number
US08937178B2

Reaction notes

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