Acetic Anhydride → 1-Acetyl-3-{1-ethoxy-1-phenylmethylidene}-5-nitro-2-indolinone

HRID 24802

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[CH2:7]2)([O-:3])=[O:2].[CH3:14][CH2:15][O:16][C:17](OCC)(OCC)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[C:30](OC(=O)C)(=[O:32])[CH3:31]>>[C:30]([N:9]1[C:10]2[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)[C:7](=[C:17]([O:16][CH2:15][CH3:14])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:8]1=[O:13])(=[O:32])[CH3:31]

Participants

Reactant 3

HCID 7918Acetic Anhydride

HCID 74268Benzene, (triethoxymethyl)-

HCID 2303665-Nitro-2-oxindole

Product 1

HCID 542801041-Acetyl-3-{1-ethoxy-1-phenylmethylidene}-5-nitro-2-indolinone

Procedure

5.07 g (23 mmol) of 5-nitro-2-indolinone are stirred for 2.5 hours at 100° C. together with 15.5 g (69 mmol) of triethyl orthobenzoate in 50 ml of acetic anhydride. After cooling, 100 ml of ether/petroleum ether (1:1) are added. The precipitate formed is suction filtered, washed with ether/petroleum ether (1:1) and dried.

Workup

temperatureAfter cooling
customThe precipitate formed
filtrationfiltered
washwashed with ether/petroleum ether (1:1)
customdried

Sources & evidence

ORD record: ord-f80aa130a7ce4fa2a1c476d0dbda6d50
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06855710B2

Linked notes

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