Potassium Carbonate → HCID 59750664, compound

HRID 422200Notes

Reaction equation

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

Participants

Reactant 3

HCID 11430Potassium Carbonate

HCID 804566-Chloronicotinamide

HCID 45759966-HYDROXY-2-TETRALONE

Product 1

HCID 59750664HCID 59750664, compoundYield 49%

Procedure

Using a method similar to Intermediate 1, using 6-hydroxy-2-tetralone (Journal of Organic Chemistry (1999), 64(26), 9719-9721) (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 (1.32 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): 8.59 (s, 1H), 8.23 (d, 1H), 8.01 (s, 1H), 7.47 (s, 1H), 7.19 (d, 2H), 7.07 (m, 2H), 6.97 (d, 1H), 3.59 (s, 2H), 3.01 (t, 2H), 2.43 (t, 2H).

Sources & evidence

ORD record: ord-9ff9e5688bfe42df807da17fde24d4be
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101638B2

Reaction notes

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