HCID 23594025, compound → HCID 23594011, compound

HRID 1612059Notes

Reaction equation

HRID 1612059 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=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[CH2:8][CH2:9][CH2:10][CH2:11][C:12]=12

Participants

3

Reactant 1

HCID 23594025HCID 23594025, compound

Product 1

HCID 23594011HCID 23594011, compoundYield 44.1%

Reagents, catalysts & solvents 1

HCID 7540Triphenyl phosphiteSolvent

Procedure

A solution of 2-(1-methoxy-5,6,7,8-tetrahydronaphthalen-2-yl)-3-nitrobenzoic acid, methyl ester, (0.5 g, 1.46 mM) in triphenyl phosphite (2.26 g, 1.91 mL, 7.29 mM) was heated at 160° C. for 48 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 10% ethyl acetate/hexane) to afford 0.2 g (44%) of the title compound 11-methoxy-7,8,9,10-tetrahydro-5H-benzo[b]carbazole-1-carboxylic acid, methyl ester as a tan solid (MP 194–196° C., MW 309.37).

Workup

  1. dry with materialdried azeotropically in vacuo with toluene
  2. custompurified by column chromatography on silica gel (elution with 10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ac3a2b81f6ea4afb80cb737100d7fb8f
Source dataset
uspto-grants-2006_01
Patent number
US06992100B2

Reaction notes

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