2-Naphthoxyacetic acid → HCID 910292, compound

HRID 2225747Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:15])[C:9]2C=CC=CC=2)=[CH:4][CH:3]=1.[CH:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][C:17]=1[O:26][CH2:27][C:28]([OH:30])=O>ClCCl.C(N(CC)CC)C.O.C(=O)(O)[O-].[Na+]>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:28](=[O:30])[CH2:27][O:26][C:17]2[CH:18]=[CH:19][C:20]3[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:16]=2)=[CH:3][CH:4]=1)(=[O:15])[CH3:9]

Participants

Conditions

Temperature: -78 °C

Procedure

A stirred mixture of para-aminobenzophenone (6.75 g) in dichloromethane (75 mL) and triethylamine (20 mL) was chilled to -78° C. and treated with the acid chloride prepared from 2-naphthoxyacetic acid (10.1 g). The mixture was stirred for 30 minutes at -78° C. and for 1 hour at room temperature. The mixture was diluted with water and sodium bicarbonate solution and the solids were recovered by filtration and washed with water and dichloromethane to give 13.3 g of N-(4-acetylphenyl)-2-naphthoxyacetamide, 208°-210° C.

Workup

filtrationthe solids were recovered by filtration
washwashed with water and dichloromethane

Sources & evidence

ORD record: ord-1576cd7376e64b958c9224d33af21e5c
Source dataset: uspto-grants-1994_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05344843

Reaction notes

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