Dimethylformamide → HCID 66649379, compound

HRID 420167Notes

Reaction equation

HRID 420167 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[C:12]([N+:17]([O-:19])=O)[C:13]=1[CH2:14][CH:15]=O)[C:6]([O:8][CH2:9][CH3:10])=[O:7].[CH3:20]N(C=O)C>[Pd]>[CH3:20][O:19][N:17]1[C:12]2[C:13](=[C:3]([O:2][CH3:1])[CH:4]=[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:11]=2)[CH:14]=[CH:15]1

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 86621577HCID 86621577, compound

Product 1

HCID 66649379HCID 66649379, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

250 mg of ethyl 3-(methoxy)-5-nitro-4-(2-oxoethyl)benzoate was dissolved in 5 ml of DMF and the solution was stirred over 50 mg of 10% Pd/C (50% wet) under hydrogen atmosphere for 6 hrs. Then the mixture was purged with N2 and 126 uL of MeI and 276 mg of K2CO3 was added thereto. After stirred for 2 hrs, the mixture was diluted with Et2O, filtered through Celite. The filtrate was concentrated and purified on SiO2 column chromatography to give 184 mg of the intended compound as colorless oil.

Workup

  1. customThen the mixture was purged with N2 and 126 uL of MeI and 276 mg of K2CO3
  2. additionwas added
  3. additionthe mixture was diluted with Et2O
  4. filtrationfiltered through Celite
  5. concentrationThe filtrate was concentrated
  6. custompurified on SiO2 column chromatography

Sources & evidence

ORD record
ord-b7240149beb941e69b06f4a3de6b8dbc
Source dataset
uspto-grants-2012_01
Patent number
US08093389B2

Reaction notes

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