2-(5-Chloro-2-nitrophenoxy)-5-methoxybenzoic acid → 1-Chloro-7-methoxy-4-nitro-9H-xanthen-9-one

HRID 364174Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:20]([O-:22])=[O:21])=[C:6]([CH:19]=1)[O:7][C:8]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:9]=1[C:10]([OH:12])=O>O>[Cl:1][C:2]1[C:19]2[C:10](=[O:12])[C:9]3[C:8](=[CH:16][CH:15]=[C:14]([O:17][CH3:18])[CH:13]=3)[O:7][C:6]=2[C:5]([N+:20]([O-:22])=[O:21])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 110 °C

Procedure

2-(5-Chloro-2-nitrophenoxy)-5-methoxybenzoic acid, 50 g, was added to 400 g of polyphosphoric acid, and the mixture stirred at 110° C. for 24 hours. The mixture was poured into 2 liters of water, and the resulting precipitate filtered to afford a light green solid. Recrystallization from dimethylformamide gave the title compound as green needles, mo 249°-251° C.

Workup

filtrationthe resulting precipitate filtered
customto afford a light green solid
customRecrystallization from dimethylformamide

Sources & evidence

ORD record: ord-d34880c459dc4c43938c4e920aab3ae5
Source dataset: uspto-grants-1986_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04604390

Reaction notes

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