4-Ethoxyaniline → HCID 15922784, compound

HRID 1731384Notes

Reaction equation

HRID 1731384 reaction equation
[CH2:1]([O:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)[CH3:2].Cl[C:12]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][C:18]([N+:24]([O-:26])=[O:25])=[C:17](Cl)[C:13]=1[C:14]([OH:16])=[O:15].C(N(CC)C(C)C)(C)C>C(#N)C>[CH2:1]([O:3][C:4]1[CH:10]=[CH:9][C:7]([NH:8][C:12]2[C:13]([C:14]([OH:16])=[O:15])=[CH:17][C:18]([N+:24]([O-:26])=[O:25])=[CH:19][C:20]=2[N+:21]([O-:23])=[O:22])=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 90764-EthoxyanilineHCID 81531DiisopropylethylamineHCID 2963442,6-dichloro-3,5-dinitrobenzoic acid

Product 1

HCID 15922784HCID 15922784, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 10.5 g of 4-ethoxyaniline in 250 ml acetonitrile was added over a 1.5 hour period to a solution of 20 g of 2,6-dichloro-3,5-dinitrobenzoic acid and 11 g of N,N-diisopropylethylamine in 400 ml of acetonitrile and stirred at room temperature for five hours. After the solvent was removed in vacuo, the residue was dissolved in 500 ml of chloroform and extracted with several portions of 5% ammonium hydroxide. The aqueous extracts were washed with chloroform and acidified with dilute acid. The resulting solid was collected by filtration and was washed with water to provide 2-chloro=6-[(4-ethoxyphenyl)amino]-3,5-dinitrobenzoic acid, mp 202°-206° C.

Workup

  1. customAfter the solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in 500 ml of chloroform
  3. extractionextracted with several portions of 5% ammonium hydroxide
  4. washThe aqueous extracts were washed with chloroform
  5. additionwith dilute acid
  6. filtrationThe resulting solid was collected by filtration
  7. washwas washed with water

Sources & evidence

ORD record
ord-5e879764cf44469795bfe00e7048f7e2
Source dataset
uspto-grants-1986_11
Patent number
US04621086

Reaction notes

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