Potassium Carbonate → 6-(7-Oxo-5,6,7,8-tetrahydro-naphthalen-2-yloxy)-nicotinamide

HRID 422199Notes

Reaction equation

HRID 422199 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:12])[CH2:9]2)=[CH:4][CH:3]=1.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:1]=[C:2]1[CH2:11][C:10]2[CH:9]=[C:8]([O:12][C:14]3[CH:22]=[CH:21][C:17]([C:18]([NH2:20])=[O:19])=[CH:16][N:15]=3)[CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3]1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 804566-ChloronicotinamideHCID 41988757-Hydroxy-2-tetralone

Product 1

HCID 597506446-(7-Oxo-5,6,7,8-tetrahydro-naphthalen-2-yloxy)-nicotinamideYield 22.7%

Procedure

Using a method similar to Example A, using 7-hydroxy-2-tetralone (1.88 g, 11.6 mmol), 6-chloronicotinamide (1.81 g, 11.6 mmol) and K2CO3 (2.40 g, 17.4 mmol) gives the title compound (742 mg), after purification on silica gel (30% THF/DCM), as an amber foam. Mass spectrum (ion spray): m/z=283 (M+1); 1HNMR (DMSO-d): 8.57 (s, 1H), 8.23 (d, 1H), 8.01 (s, 1H), 7.46 (s, 1H), 7.30 (d, 2H), 7.05 (d, 1H), 6.96 (m, 2H), 3.59 (s, 2H), 3.02 (t, 2H), 2.45 (t, 2H).

Sources & evidence

ORD record
ord-a1a11517c824407fb355d4e86848297b
Source dataset
uspto-grants-2012_01
Patent number
US08101638B2

Reaction notes

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