3-Nitroaniline → Butanamide, N-(3-nitrophenyl)-

HRID 1484535Notes

Reaction equation

HRID 1484535 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])([O-:3])=[O:2].CCN(C(C)C)C(C)C.[C:20](Cl)(=[O:24])[CH2:21][CH2:22][CH3:23]>ClCCl>[N+:1]([C:4]1[CH:5]=[C:6]([NH:7][C:20](=[O:24])[CH2:21][CH2:22][CH3:23])[CH:8]=[CH:9][CH:10]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 74233-NitroanilineHCID 8855Butyryl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 346258Butanamide, N-(3-nitrophenyl)-Yield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Nitroaniline (6.00 g, 43.4 mmol) was sealed in a flask with stir bar under nitrogen and dissolved with dichloromethane (DCM, 145 mL). The solution was cooled on ice before (i-Pr)2NEt (8.35 ml, 47.8 mmol) and butyryl chloride (5.00 ml, 47.8 mmol) were added. The flask was removed from the ice and stirred for 16 h. The reaction was then diluted with DCM and aq. 1 M HCl, the layers were separated, and the combined organics were washed again with 1 M aq. HCl, then twice with half-saturated aq. NaHCO3, then brine. The organic phase was dried over MgSO4, filtered, and concentrated, yielding a yellow oil (9.04 g, 100%). LRMS (ESI−) (M−H): 207.06. The crude oil was used without further purification in the subsequent reaction.

Workup

  1. additionwere added
  2. customThe flask was removed from the ice
  3. stirringstirred for 16 h
  4. additionThe reaction was then diluted with DCM and aq. 1 M HCl
  5. customthe layers were separated
  6. washthe combined organics were washed again with 1 M aq. HCl
  7. dry with materialThe organic phase was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-dcd2f4e18ce043078180de5dd6303cd0
Source dataset
uspto-grants-2016_08
Patent number
US09422262B2

Reaction notes

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