2-(5-Nitro-2-allyloxyphenyl)-5-phenylbenzoxazole → 2-(5-Amino-2-allyloxyphenyl)-5-phenylbenzoxazole

HRID 722532Notes

Reaction equation

HRID 722532 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:25][CH2:26][CH:27]=[CH2:28])=[C:8]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:15][C:13]=3[N:14]=2)[CH:9]=1)([O-])=O>C(O)(=O)C.[Zn]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:25][CH2:26][CH:27]=[CH2:28])=[C:8]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:15][C:13]=3[N:14]=2)[CH:9]=1

Participants

4

Reactant 1

HCID 218845392-(5-Nitro-2-allyloxyphenyl)-5-phenylbenzoxazole

Product 1

HCID 218843082-(5-Amino-2-allyloxyphenyl)-5-phenylbenzoxazoleYield 172.2%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Powdered zinc (377 mg, 5.8 mmol) was added to a solution of 2-(5-nitro-2-allyloxyphenyl)-5-phenylbenzoxazole (216 mg, 0.58 mmol) in acetic acid (2 ml). After 2 h the reaction mixture was filtered through celite and the filtrate concentrated. The residue was dissolved in ethyl acetate (10 ml) and washed with saturated sodium hydrogen carbonate solution (2×25 ml). The organic layer was dried over sodium sulfate and concentrated to give the subtitle compound (342 mg, 100%). The product was used directly in the next step without purification.

Workup

  1. filtrationAfter 2 h the reaction mixture was filtered through celite
  2. concentrationthe filtrate concentrated
  3. dissolutionThe residue was dissolved in ethyl acetate (10 ml)
  4. washwashed with saturated sodium hydrogen carbonate solution (2×25 ml)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-dca02115c2024aadbdb58170a067760c
Source dataset
uspto-grants-2006_11
Patent number
US07138425B2

Reaction notes

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