HCID 57465372, compound → HCID 57465373, compound

HRID 1951580Notes

Reaction equation

HRID 1951580 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=2)=[N:4][C:3]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(O)(=O)C.[Zn]>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]([NH2:13])=[CH:11][CH:12]=2)=[N:4][C:3]=1[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 1

HCID 57465372HCID 57465372, compound

Product 1

HCID 57465373HCID 57465373, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

to a suspension of 5-methyl-2-(4-nitrophenyl)-4-phenyloxazole (1.20 g, 4.3 mmol) in acetic acid at room temperature was added all at once zinc dust (0.59 ml, 64 mmol). An exotherm developed. The mixture was stirred vigorously for 90 minutes then filtered. The filtrate was concentrated under reduced pressure, diluted with toluene then concentrated under reduced pressure to afford a yellow oily solid (1.1 g, quant.). ESI+ m/z=251.1 [MH]+.

Workup

  1. filtrationthen filtered
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. additiondiluted with toluene
  4. concentrationthen concentrated under reduced pressure
  5. customto afford a yellow oily solid (1.1 g, quant.)

Sources & evidence

ORD record
ord-2bb216e982204ed4be9e589072b9ef81
Source dataset
uspto-grants-2013_03
Patent number
US08404722B2

Reaction notes

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