Sodium Hydroxide → 3-(6-Dimethylamino-3-methyl-benzofuran-2-yl)-3-(2-methyl-1-n-octylindol-3-yl)phthalide

HRID 2352355Notes

Reaction equation

[CH3:1][C:2]1[N:3]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C:4]2[C:9]([C:10]=1[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]([OH:21])=[O:20])=O)=[CH:8][CH:7]=[CH:6][CH:5]=2.[CH3:30][N:31]([CH3:42])[C:32]1[CH:41]=[CH:40][C:35]2[C:36]([CH3:39])=[CH:37][O:38][C:34]=2[CH:33]=1.[OH-].[Na+]>C(OC(=O)C)(=O)C>[CH3:42][N:31]([CH3:30])[C:32]1[CH:41]=[CH:40][C:35]2[C:36]([CH3:39])=[C:37]([C:11]3([C:10]4[C:9]5[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=5)[N:3]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C:2]=4[CH3:1])[C:13]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:19](=[O:21])[O:20]3)[O:38][C:34]=2[CH:33]=1

Participants

Conditions

Temperature: 40 °C

Procedure

3.5 g of (2-methyl-1-n-octylindol-3-yl)-(2-carboxyphenyl)ketone and 1.6 g of 6-dimethylamino-3-methylbenzofuran are suspended in 45 ml of acetic anhydride and heated to 40° C. After 2 hours the reaction product is poured onto ice, basified with concentrated sodium hydroxide solution and filtered off. The crude product is recrystallized from toluene/methanol to give 3.25 g of the 3-(6-dimethylamino-3-methyl-benzofuran-2-yl)-3-(2-methyl-1-n-octylindol-3-yl)phthalide compound of the formula ##STR25## having a melting point of 157°-158° C. The phthalide compound gives a green colour on acid-modified silica gel.

Workup

additionAfter 2 hours the reaction product is poured onto ice
filtrationfiltered off
customThe crude product is recrystallized from toluene/methanol

Sources & evidence

ORD record: ord-b4d021a159884fd8932ec5a64d51ea4e
Source dataset: uspto-grants-1989_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04876357

Reaction notes

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