HCID 23594024, compound → HCID 23594015, compound

HRID 1612050Notes

Reaction equation

HRID 1612050 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[C:13]1[C:22]([N+:23]([O-])=O)=[CH:21][CH:20]=[CH:19][C:14]=1[C:15]([O:17][CH3:18])=[O:16]>P(OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1>[CH3:1][O:2][C:3]1[C:4]2[C:13]3[C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:19][CH:20]=[CH:21][C:22]=3[NH:23][C:5]=2[CH:6]=[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=12

Participants

3

Reactant 1

HCID 23594024HCID 23594024, compound

Product 1

HCID 23594015HCID 23594015, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 7540Triphenyl phosphiteSolvent

Procedure

A solution of 2-(1-methoxynaphthalen-2-yl)-3-nitrobenzoic acid, methyl ester, (1.52 g, 4.5 mM) in triphenyl phosphite (7.19 g, 6.1 mL, 22.5 mM) was heated at 160° C. for 19 h under a nitrogen atmosphere. The mixture was cooled to room temperature and dried azeotropically in vacuo with toluene, then purified by column chromatography on silica gel (elution with gradient hexane/ethyl acetate) to afford 0.37 g (27%) of the title compound 11-methoxy-5H-benzo[b]carbazole-1-carboxylic acid, methyl ester as a yellow solid (MP 190–196° C., MW 305.34).

Workup

  1. dry with materialdried azeotropically in vacuo with toluene
  2. custompurified by column chromatography on silica gel (elution with gradient hexane/ethyl acetate)

Sources & evidence

ORD record
ord-79f2c42c834e47e78c6da09bff5072a1
Source dataset
uspto-grants-2006_01
Patent number
US06992100B2

Reaction notes

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