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

HRID 1833305Notes

Reaction equation

HRID 1833305 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][CH3:29].C(N(CC)CC)C.Cl>O>[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][CH3:29])([OH:6])=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 172872-Chloro-5-nitrobenzoic acidHCID 122360N-Methyltetradecylamine

Product 1

HCID 213887262-[Methyl(tetradecyl)amino]-5-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 600g 2-chloro-5-nitrobenzoic acid, 900g methyltetradecylamine (84%, tertiary amines as impurities) and 500 ml triethylamine was heated on a steam bath for 7 hours and then poured into 2 liters of water and made acid with HCl. The reaction product was filtered, air dried and then recrystallized from methanol and then from petroleum ether. Yield: 820g, m.p. = 100°-101°.

Workup

  1. temperaturewas heated on a steam bath for 7 hours
  2. filtrationThe reaction product was filtered
  3. customair dried
  4. customrecrystallized from methanol

Sources & evidence

ORD record
ord-4a32c4d9c5f648599feb949022dad68c
Source dataset
uspto-grants-1978_01
Patent number
US04066456

Reaction notes

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