Acetic Anhydride → HCID 14149590, compound

HRID 648804Notes

Reaction equation

HRID 648804 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](O)=[O:18])=[O:14].[CH2:24]([O:26][CH2:27][CH2:28][N:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=[C:30]1[CH3:38])[CH3:25].[C:39](OC(=O)C)(=O)C.[OH-].[NH4+]>CCCCCC.C1(C)C=CC=CC=1>[CH2:24]([O:26][CH2:27][CH2:28][N:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31]([C:13]2([C:3]3[CH:4]=[CH:5][C:6]([N:8]([CH2:11][CH3:12])[CH2:9][CH3:10])=[CH:7][C:2]=3[CH2:1][CH3:39])[C:15]3[C:16](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:17](=[O:18])[O:14]2)=[C:30]1[CH3:38])[CH3:25]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 14923Ammonium HydroxideHCID 1043352-(4-(Diethylamino)-2-methylbenzoyl)benzoic acidHCID 21284000HCID 21284000, compound

Product 1

HCID 14149590HCID 14149590, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

A mixture of 14.5 g of 2-(2-methyl-4-diethylaminophenyl)carbonylbenzoic acid (68.5 percent active). 9.0 g of 1-(2-ethoxyethyl) 2-methylindole and 60.0 ml acetic anhydride was maintained at approximately 70° C. for approximately three hours. After cooling to ambient temperature, the reaction solution was poured slowly into a mixture of toluene and 5 percent aqueous ammonium hydroxide. The toluene layer was separated and evaporated to dryness to obtain a gummy residue. The residue was triturated with hexane and the solid which separated was isolated by filtration. The solid was reslurried in 300.0 ml of hot hexane, filtered, and dried to obtain 11.5 g of 3-[1-(2-ethoxyethyl)-2-methylindol-3-yl]-3-(2-ethyl-4-diethylaminophenyl)phthalide (Formula I: R=C2H5OC2H4 ; R1 =R2 =CH3 ; R3 =R4 =C2H5 ; X=Y=H), a pale pink-colored solid which melted at 156°-158° C. Significant infrared maxima appeared at 1765 (C=O; s) and 1120 (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 developed a cyan-colored image.

Workup

  1. customThe toluene layer was separated
  2. customevaporated to dryness
  3. customto obtain a gummy residue
  4. customThe residue was triturated with hexane
  5. customthe solid which separated
  6. customwas isolated by filtration
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-d8b2591f524b4bab882f2d256b988d4e
Source dataset
uspto-grants-1988_04
Patent number
US04736027

Reaction notes

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