Potassium Carbonate → 6-(6-Oxo-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-nicotinamide

HRID 422201Notes

Reaction equation

HRID 422201 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][C:6](=[O:12])[CH2:7]2.Cl[C:14]1[CH:22]=[CH:21][C:17]([C:18]([NH2:20])=[O:19])=[CH:16][N:15]=1.C([O-])([O-])=O.[K+].[K+]>>[O:12]=[C:6]1[CH2:5][CH2:4][C:3]2[C:2]([O:1][C:14]3[CH:22]=[CH:21][C:17]([C:18]([NH2:20])=[O:19])=[CH:16][N:15]=3)=[CH:11][CH:10]=[CH:9][C:8]=2[CH2:7]1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 804566-ChloronicotinamideHCID 51035275-Hydroxy-2-tetralone

Product 1

HCID 597506766-(6-Oxo-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-nicotinamideYield 52.7%

Procedure

Using a method similar to Intermediate 1, using 5-hydroxy-2-tetralone (J. Med. Chem. (1978), 21(9), 913-22) (1.98 g, 12.1 mmol), 6-chloronicotinamide (1.90 g, 12.1 mmol) and K2CO3 (2.52 g, 18.2 mmol) gives the title compound (1.80 g), after purification on silica gel (50% THF/DCM), as an amber foam. Mass spectrum (ion spray): m/z=283 (M+1); 1HNMR (DMSO-d6): 8.55 (s, 1H), 8.24 (d, 1H), 8.00 (s, 1H), 7.46 (s, 1H), 7.25 (d, 2H), 7.08 (m, 2H), 7.00 (d, 1H), 3.64 (s, 2H), 2.77 (t, 2H), 2.34 (t, 2H).

Sources & evidence

ORD record
ord-6c6bf4fcffaf4ca2882e92a35c842103
Source dataset
uspto-grants-2012_01
Patent number
US08101638B2

Reaction notes

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