3-Nitroaniline → 3-chloro-N-(3-nitrophenyl)propanamide

HRID 716854Notes

Reaction equation

HRID 716854 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])([O-:3])=[O:2].[Cl:11][CH2:12][CH2:13][C:14](Cl)=[O:15]>C1COCC1>[Cl:11][CH2:12][CH2:13][C:14]([NH:7][C:6]1[CH:8]=[CH:9][CH:10]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)=[O:15]

Participants

4

Reactant 2

HCID 74233-NitroanilineHCID 693643-Chloropropionyl chloride

Product 1

HCID 34652363-chloro-N-(3-nitrophenyl)propanamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 3-nitroaniline (37a, 6.9 g, 50 mmol) in THF (50 mL) was added dropwise 3-chloropropionyl chloride (10 mL, 100 mmol) over 30 min under argon atmosphere. The reaction was stirred at 50° C. for 10 h. After cooling, the reaction mixture was evaporated to dryness under vacuo and the residue was neutralized with saturated aqueous solution of NaHCO3 and the solid product was collected by filtration, washed with water followed by hexane, and dried to afford 3-chloro-N-(3-nitrophenyl)propanamide, 10.61 g (92%), mp 86-88° C. (Lit. 100-102° C.57). 1H NMR (DMSO-d6) δ: 2.87-2.90 (2H, t, J=9.9 Hz, CH2), 3.90-3.92 (2H, t, J=9.9 Hz, CH2), 7.61-7.64 (1H, t, J=6.6 and 6.6 Hz, Ar—H), 7.90-7.94 (2H, m, Ar—H), 8.65-8.66 (1H, t, J=3.4 and 1.7 Hz, Ar—H), 10.59 (1H, brs, NH).

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture was evaporated to dryness under vacuo
  3. filtrationthe solid product was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-62019b26578c45fa93f418931b53bffc
Source dataset
uspto-grants-2015_11
Patent number
US09193687B2

Reaction notes

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