HCID 53787386, compound → HCID 54489315, compound

HRID 1065822Notes

Reaction equation

HRID 1065822 reaction equation
[CH2:1]([NH:11][C:12](=[O:24])[CH:13]=[CH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-])=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]>[Fe].C(O)(=O)C>[CH2:1]([NH:11][C:12](=[O:24])[CH:13]=[CH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH2:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

4

Reactant 1

HCID 53787386HCID 53787386, compound

Product 1

HCID 54489315HCID 54489315, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

A stirred solution of 15.3 g. of N-decyl-3-(2-nitrophenyl)propenamide in 200 ml. of glacial acetic acid was heated to 85° C. on a steam bath, and then 12.9 g. of iron powder was added portionwise, during 25 minutes. The reaction temperature was kept between 85° and 95° C. during the addition. The reaction mixture was filtered hot, and the residue was washed with hot glacial acetic acid. The cooled, combined acetic acid solutions were evaporated in vacuo, and the residue was dissolved in ethyl acetate. The ethyl acetate solution was washed several times with water and then with saturated sodium chloride solution. The resulting solution was dried using sodium sulfate, and then it was evaporated in vacuo to give the crude title product.

Workup

  1. additionThe reaction temperature was kept between 85° and 95° C. during the addition
  2. filtrationThe reaction mixture was filtered hot
  3. washthe residue was washed with hot glacial acetic acid
  4. customwere evaporated in vacuo
  5. dissolutionthe residue was dissolved in ethyl acetate
  6. washThe ethyl acetate solution was washed several times with water
  7. customThe resulting solution was dried
  8. customit was evaporated in vacuo

Sources & evidence

ORD record
ord-d40d3b816e444fefade35da0d7179410
Source dataset
uspto-grants-1982_05
Patent number
US04331683

Reaction notes

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