Hydrochloric Acid → 2-[Methyl(octadecyl)amino]-5-nitrobenzoic acid

HRID 1833307Notes

Reaction equation

HRID 1833307 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:14][NH: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][CH2:32][CH3:33].C(N(CC)CC)C.Cl>C(O)C>[C:4]([C:3]1[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=[CH:10][C:2]=1[N:15]([CH3:14])[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][CH2:32][CH3:33])([OH:6])=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 172872-Chloro-5-nitrobenzoic acidHCID 75539N-Methyloctadecylamine

Product 1

HCID 213887322-[Methyl(octadecyl)amino]-5-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 20g 2-chloro-5-nitrobenzoic acid, 28.6g methyl octadecylamine and 20 ml triethylamine was heated on a steam bath for 6 hours. The resulting solid was dissolved in aqueous ethanol, and then 6N HCl was added to give a pH of 3. The product was filtered and recrystallized from ethanol and then from acetone. m.p. = 108°-109°.

Workup

  1. temperaturewas heated on a steam bath for 6 hours
  2. customto give a pH of 3
  3. filtrationThe product was filtered
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-fa793bdeb2404a46baf3bb8a5b3499ec
Source dataset
uspto-grants-1978_01
Patent number
US04066456

Reaction notes

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