Acetic Anhydride → HCID 14149594, compound

HRID 543030Notes

Reaction equation

HRID 543030 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N:8]([CH2:11][CH3:12])[CH2:9][CH3:10])[CH:5]=[CH:4][C:3]=1[C:13]([C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17]([OH:19])=O)=[O:14].[O:24]([CH2:31][CH2:32][N:33]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:35]=[C:34]1[CH3:42])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(OC(=O)C)(=O)C.[OH-].[NH4+]>C1(C)C=CC=CC=1.C(O)(C)C>[O:24]([CH2:31][CH2:32][N:33]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:35]([C:13]2([C:3]3[CH:4]=[CH:5][C:6]([N:8]([CH2:9][CH3:10])[CH2:11][CH3:12])=[CH:7][C:2]=3[CH3:1])[C:15]3[C:16](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:17](=[O:19])[O:14]2)=[C:34]1[CH3:42])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 14923Ammonium HydroxideHCID 1043352-(4-(Diethylamino)-2-methylbenzoyl)benzoic acidHCID 14178120HCID 14178120, compound

Product 1

HCID 14149594HCID 14149594, compoundYield 93.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 14.0 g of 2-(2-methyl-4-diethylaminophenyl)carbonylbenzoic acid, 10.0 g of 1-(2-phenoxyethyl)-2-methylindole and 500.0 ml of acetic anhydride was maintained at approximately 70° C. for approximately four hours. The reaction solution was cooled to ambient temperature and 25.0 ml of isopropyl alcohol was added. The resulting solution was poured slowly into a mixture of 500.0 ml of toluene and 50.0 ml of 5 percent aqueous ammonium hydroxide. The toluene layer was separated, washed with water and then with saturated aqueous sodium chloride solution. The toluene layer was evaporated to dryness. The residue was recrystallized in 150.0 ml of isopropyl alcohol and dried to obtain 20.2 g of 3-[1-(2-phenoxyethyl)-2-methylindol-3-yl]-3-(2-methyl-4-diethylaminophenyl)phthalide (Formula I: R=C6H5OC2H4 ; R1 =R2 =CH3 ; R3 =R4 =C2H5 ; X=Y=H), a white-colored solid which melted at 182°-183° C. Significant infrared maxima appeared at 1750 (C=O;s) and 1130 (C--O;s)cm-1. The nuclear magnetic resonance spectrum was in accord with the assigned structure. A toluene solution of the product spotted on an acidic clay or a phenolic resin coated paper developed a cyan-colored image.

Workup

  1. temperatureThe reaction solution was cooled to ambient temperature
  2. customThe toluene layer was separated
  3. washwashed with water
  4. customThe toluene layer was evaporated to dryness
  5. customThe residue was recrystallized in 150.0 ml of isopropyl alcohol
  6. customdried

Sources & evidence

ORD record
ord-4b6b826369d9494eb948dad07f70b344
Source dataset
uspto-grants-1987_04
Patent number
US04660060

Reaction notes

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