1H-Indole, 1-ethyl-2-methyl- → 2-(1-Ethyl-2-methyl-1H-indole-3-carbonyl)-5-nitrobenzoic acid

HRID 1413874Notes

Reaction equation

HRID 1413874 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[O:10][C:8](=[O:9])[C:7]2=[CH:13][CH:14]=1)([O-:3])=[O:2].[CH2:15]([N:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[C:18]1[CH3:26])[CH3:16]>C(Cl)CCl>[CH2:15]([N:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]([C:8]([C:7]2[CH:13]=[CH:14][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=2[C:11]([OH:10])=[O:12])=[O:9])=[C:18]1[CH3:26])[CH3:16]

Participants

4

Reactant 2

HCID 1704321H-Indole, 1-ethyl-2-methyl-HCID 2309764-Nitrophthalic acid anhydride

Product 1

HCID 205235612-(1-Ethyl-2-methyl-1H-indole-3-carbonyl)-5-nitrobenzoic acidYield 57.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 67.2 g (0.4 mole) of 4-nitrophthalic anhydride and 63.0 g (0.32 mole) of 80.6 percent active 1-ethyl-2-methylindole in 50 ml of ethylene dichloride was heated at reflux for two hours. The reaction mixture was then allowed to cool to room temperature. The yellow precipitate which separated was collected by filtration, washed with fresh ethylene dichloride and dried to obtain 64.5 g of 2-[(1-ethyl-2-methyl-3-indolyl)carbonyl]-5-nitrobenzoic acid (Formula VIII: R0 =R2 =R3 =Y1 =H; R1 =NO2 ; R5 =CH3 ; R6 =CH2CH3) having a melting point of 203°-204° C.

Workup

  1. temperatureat reflux for two hours
  2. customThe yellow precipitate which separated
  3. filtrationwas collected by filtration
  4. washwashed with fresh ethylene dichloride
  5. customdried

Sources & evidence

ORD record
ord-5382bf4bc9014348af5f5f7d3430425f
Source dataset
uspto-grants-1981_02
Patent number
US04251446

Reaction notes

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