Isopropanol → 7-({2-[(4-Methoxybenzyl)amino]pyridin-4-yl}oxy)-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid

HRID 1640123Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:31]=[CH:30][C:6]([CH2:7][NH:8][C:9]2[CH:14]=[C:13]([O:15][C:16]3[CH:25]=[C:24]4[C:19]([CH2:20][CH2:21][CH:22]([C:26]([OH:28])=[O:27])[CH2:23]4)=[CH:18][CH:17]=3)[CH:12]=[CH:11][N+:10]=2[O-])=[CH:5][CH:4]=1.C(O)(C)C>[Pd].C1CCCCC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][NH:8][C:9]2[CH:14]=[C:13]([O:15][C:16]3[CH:25]=[C:24]4[C:19]([CH2:20][CH2:21][CH:22]([C:26]([OH:28])=[O:27])[CH2:23]4)=[CH:18][CH:17]=3)[CH:12]=[CH:11][N:10]=2)=[CH:30][CH:31]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of 7-({2-[(4-methoxybenzyl)amino]-1-oxidopyridin-4-yl}oxy)-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid (21.1 g, 0.0502 mol), cyclohexene (100 mL, 0.9 mol) and Pd (10% on Carbon, 4.5 g) in isopropyl alcohol (400 mL, 5 mol) was heated at 85° C. overnight. Additional catalyst (2.5 g) and cyclohexene (30 mL) were added. The mixture was heated at 90° C. overnight and then filtered. The filtrate was concentrated to give 7-({2-[(4-methoxybenzyl)amino]pyridin-4-yl}oxy)-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid which was used in the next step without purification. LCMS ES+ 405.7

Workup

temperatureThe mixture was heated at 90° C. overnight
filtrationfiltered
concentrationThe filtrate was concentrated

Sources & evidence

ORD record: ord-e79e74c481414470aec1b7e2b799dffb
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08110687B2

Reaction notes

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