Water → Benzoic acid, 2-[(1-ethyl-2-methyl-1H-indol-3-yl)carbonyl]-

HRID 1449081Notes

Reaction equation

HRID 1449081 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=[O:5])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[CH2:12]([N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[C:15]1[CH3:23])[CH3:13].[Cl-].[Al+3].[Cl-].[Cl-].O>C(Cl)CCl>[CH2:12]([N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([C:4]([C:3]2[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=2[C:1]([OH:6])=[O:11])=[O:5])=[C:15]1[CH3:23])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 6811Phthalic AnhydrideHCID 1704321H-Indole, 1-ethyl-2-methyl-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 3084978Benzoic acid, 2-[(1-ethyl-2-methyl-1H-indol-3-yl)carbonyl]-Yield 52.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a stirred suspension of 22.5 g (0.15 mole) of phthalic anhydride and 61.0 g (0.30 mole) of 77.5 percent active 1-ethyl-2-methylindole in 120 ml of ethylene dichloride chilled to 0° to 5° C. by means of an ice bath, there was added in small portions 32.0 g (0.24 mole) of aluminum chloride. The mixture was maintained at 0°-5° C. for an additional 15 minutes, allowed to warm to room temperature and stirred overnight. Then, 240 ml of water was added to the reaction mixture and the ethylene dichloride layer was separated from the acidic aqueous layer. The organic layer was extracted with 600 ml of 3.5 percent aqueous sodium hydroxide. The alkaline extract was acidified with dilute hydrochloric acid and the separated solid collected, washed with water and dried to obtain 24.0 g of 2-[(1-ethyl-2-methyl-3-indolyl)carbonyl]benzoic acid (Formula VIII: R°=R1 =R2 = R3 =Y1 =H; R5 =CH3 ; R6 =CH2CH3), a slightly pink solid having a melting point of 184°-185° C.

Workup

  1. temperaturechilled to 0° to 5° C. by means of an ice bath
  2. temperatureThe mixture was maintained at 0°-5° C. for an additional 15 minutes
  3. customthe ethylene dichloride layer was separated from the acidic aqueous layer
  4. extractionThe organic layer was extracted with 600 ml of 3.5 percent aqueous sodium hydroxide
  5. extractionThe alkaline extract
  6. customthe separated solid collected
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-d811f980b40646f39f87fab8b2450aa4
Source dataset
uspto-grants-1980_02
Patent number
US04189171

Reaction notes

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