2'-Chloro-4'-nitrovaleranilide → N-(4-amino-2-chlorophenyl)pentanamide

HRID 46495

Reaction equation

HRID 46495 reaction equation
[Cl:1][C:2]1[CH:14]=[C:13]([N+:15]([O-])=O)[CH:12]=[CH:11][C:3]=1[NH:4][C:5](=[O:10])[CH2:6][CH2:7][CH2:8][CH3:9]>C(O)(=O)C.[Fe]>[NH2:15][C:13]1[CH:12]=[CH:11][C:3]([NH:4][C:5](=[O:10])[CH2:6][CH2:7][CH2:8][CH3:9])=[C:2]([Cl:1])[CH:14]=1

Participants

4

Reactant 1

HCID 36282822'-Chloro-4'-nitrovaleranilide

Product 1

HCID 4257591N-(4-amino-2-chlorophenyl)pentanamide

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

2'-Chloro-4'-nitrovaleranilide (13.0 g.) is dissolved in warm glacial acetic acid (100 ml.) and iron powder (14 g.) is added portionwise to maintain gentle boiling. The resulting reaction mixture is refluxed for one-half hour and filtered. The filtrate is evaporated under reduced pressure and the residue is triturated with water. The solid that forms is collected (11.5 g.) and recrystallized from cyclohexane to yield 7.5 g., m.p. 96.5°-99° C.

Workup

  1. temperatureto maintain gentle boiling
  2. customThe resulting reaction mixture
  3. temperatureis refluxed for one-half hour
  4. filtrationfiltered
  5. customThe filtrate is evaporated under reduced pressure
  6. customthe residue is triturated with water
  7. customThe solid that forms is collected (11.5 g.)
  8. customrecrystallized from cyclohexane
  9. customto yield 7.5 g

Sources & evidence

ORD record
ord-b58934a5907f46ceb67f31a793b7aafc
Source dataset
uspto-grants-1979_11
Patent number
US04173646

Linked notes

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