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

HRID 747952Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][C:9](=[O:12])[CH2:8][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:9]1[CH2:10][C:11]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:3][CH:4]=[CH:5][C:6]=2[CH2:7][CH2:8]1

Participants

Reactant 3

HCID 11430Potassium Carbonate

HCID 804566-Chloronicotinamide

HCID 5777668-Hydroxy-2-tetralone

Product 1

HCID 597506966-(7-Oxo-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-nicotinamide

Procedure

Using a method similar to Intermediate 1, using 8-hydroxy-2-tetralone (J. Med. Chem. (1978), 21(9), 913-22.) (1.55 g, 9.55 mmol), 6-chloronicotinamide (1.49 g, 9.55 mmol) and K2CO3 (1.98 g, 14.3 mmol) gives the title compound (652 mg),after purification on silica gel (50% THF/DCM), as an yellow foam. Mass spectrum (ion spray): m/z=283 (M+1); 1HNMR (CDCl3): 8.52 (s, 1H), 8.18 (d, 1H), 7.30 (t, 1H), 7.17 (d, 1H), 7.02 (m, 2H), 5.92 (broad, 2H), 3.42 (s, 2H), 3.15 (t, 2H), 2.61 (t, 2H).

Workup

customgives
customthe title compound (652 mg),after purification on silica gel (50% THF/DCM)

Sources & evidence

ORD record: ord-78168d13f8c74f82bef0a84f7cf7c7bd
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07399774B2

Reaction notes

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