Trifluoroacetic acid → 3-Nitro-5-(octadecyloxy)benzenamine

HRID 1110275Notes

Reaction equation

HRID 1110275 reaction equation
CC(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH:11]=[C:10]([N+:33]([O-:35])=[O:34])[CH:9]=1)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[N+:33]([C:10]1[CH:9]=[C:8]([NH2:7])[CH:13]=[C:12]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH:11]=1)([O-:35])=[O:34]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 542156373-Nitro-5-(octadecyloxy)phenylcarbamic acid dimethylethyl ester

Product 1

HCID 193889173-Nitro-5-(octadecyloxy)benzenamineYield 97.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4.6 g of 3-nitro-5-(octadecyloxy)phenylcarbamic acid dimethylethyl ester in 100 ml of methylene chloride stirred at room temperature was added 20 ml of trifluoroacetic acid. The reaction mixture was kept at room temperature for 3.5 hours and the solvent was then removed at reduced pressure. The residue was treated with water and the product was filtered and recrystallized from ethyl acetate-hexane to give 3.6 g (97% yield, mp 106°-108°) of 3-nitro-5-(octadecyloxy)benzenamine.

Workup

  1. customthe solvent was then removed at reduced pressure
  2. additionThe residue was treated with water
  3. filtrationthe product was filtered
  4. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-764e591615eb4e7e9f14c84d111a4186
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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