Hydrochloric Acid → 4-Ethoxy-2-[methyl(tetradecyl)amino]-5-nitrobenzoic acid

HRID 1833306Notes

Reaction equation

HRID 1833306 reaction equation
Cl[C:2]1[CH:10]=[C:9]([O:11][CH2:12][CH3:13])[C:8]([N+:14]([O-:16])=[O:15])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:17][NH: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].C(N(CC)CC)C.Cl>O>[C:4]([C:3]1[CH:7]=[C:8]([N+:14]([O-:16])=[O:15])[C:9]([O:11][CH2:12][CH3:13])=[CH:10][C:2]=1[N:18]([CH3:17])[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])([OH:6])=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 122360N-MethyltetradecylamineHCID 213887222-Chloro-4-ethoxy-5-nitrobenzoic acid

Product 1

HCID 213887294-Ethoxy-2-[methyl(tetradecyl)amino]-5-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 24.5g 2-chloro-4-ethoxy-5-nitrobenzoic acid, 22.7g methyl tetradecylamine (distilled) and 35.0 ml triethylamine were heated on a steam bath for 5 hours and then poured into two liters of water and made acid with HCl. The reaction product was filtered and washed with water, and recrystallized twice from methanol/water.

Workup

  1. temperaturewere heated on a steam bath for 5 hours
  2. filtrationThe reaction product was filtered
  3. washwashed with water
  4. customrecrystallized twice from methanol/water

Sources & evidence

ORD record
ord-67369f4a00954b118330695f3999766d
Source dataset
uspto-grants-1978_01
Patent number
US04066456

Reaction notes

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