Acetic Anhydride → HCID 14149593, compound

HRID 543029Notes

Reaction equation

HRID 543029 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[C:11]([C:13]1[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=1[C:15]([OH:17])=[O:16])=O.[CH2:22]([O:24][CH2:25][CH2:26][N:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[C:28]1[CH3:36])[CH3:23].C(OC(=O)C)(=O)C.[OH-].[NH4+]>C1(C)C=CC=CC=1>[CH2:22]([O:24][CH2:25][CH2:26][N:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29]([C:11]2([C:3]3[CH:4]=[CH:5][C:6]([N:8]([CH3:9])[CH3:10])=[CH:7][C:2]=3[CH3:1])[C:13]3[C:14](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:15](=[O:17])[O:16]2)=[C:28]1[CH3:36])[CH3:23]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 14923Ammonium HydroxideHCID 15519329HCID 15519329, compoundHCID 21284000HCID 21284000, compound

Product 1

HCID 14149593HCID 14149593, compoundYield 37.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 14.5 g of 2-(2-methyl-4-dimethylaminophenyl)carbonylbenzoic acid, 11.5 g of 1-(2-ethoxyethyl)-2-methylindole and 40.0 ml acetic anhydride was maintained at approximately 70° C. for approximately four hours. The resulting solution was cooled to ambient temperature and slowly poured into a mixture of toluene and 5 percent aqueous ammonium hydroxide. The toluene layer was separated, washed with water and then with saturated sodium chloride solution. The toluene solution was evaporated to dryness. The residue which remained was recrystallized twice from a mixture of hexane and isopropyl alcohol to obtain 8.9 g of 3-[1-(2-ethoxyethyl)-2-methylindol-3-yl]-3-(2-methyl-4-dimethylaminophenyl)phthalide (Formula I: R=C2H5OC2H4 ; R1 =R2 =R3 =R4 =CH3 ; X=Y=H), a white-colored solid which melted at 170.5° to 171° C. Significant infrared maxima appeared at 1750 (C=O;s) and 1123 (C--O;s)cm-1. A toluene solution of the product spotted on an acid clay or a phenolic resin coated paper developed a cyan-colored image.

Workup

  1. temperatureThe resulting solution was cooled to ambient temperature
  2. customThe toluene layer was separated
  3. washwashed with water
  4. customThe toluene solution was evaporated to dryness
  5. customThe residue which remained was recrystallized twice from a mixture of hexane and isopropyl alcohol

Sources & evidence

ORD record
ord-8d7829aa13f8402b9fb1080b640d5639
Source dataset
uspto-grants-1987_04
Patent number
US04660060

Reaction notes

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