Potassium Carbonate → 1,2,3,4-Tetrahydro-3-(phenylmethyl)-8-[(1-phenyl-1H-tetrazol-5-yl)oxy]-5H-[1]benzopyrano[3,4-c]pyridin-5-one

HRID 851232Notes

Reaction equation

HRID 851232 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[CH2:13][CH2:12][N:11]([CH2:14][C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[CH2:10][C:9]=3[C:21](=[O:23])[O:22][C:4]=2[CH:3]=1.Cl[C:25]1[N:29]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:28]=[N:27][N:26]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:15]1([CH2:14][N:11]2[CH2:12][CH2:13][C:8]3[C:5]4[CH:6]=[CH:7][C:2]([O:1][C:25]5[N:29]([C:30]6[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=6)[N:28]=[N:27][N:26]=5)=[CH:3][C:4]=4[O:22][C:21](=[O:23])[C:9]=3[CH2:10]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 842621H-Tetrazole, 5-chloro-1-phenyl-HCID 133817811,2,3,4-Tetrahydro-8-hydroxy-3-(phenylmethyl)5H-[1]benzopyrano[3,4-c]pyridin-5-one

Product 1

HCID 133817821,2,3,4-Tetrahydro-3-(phenylmethyl)-8-[(1-phenyl-1H-tetrazol-5-yl)oxy]-5H-[1]benzopyrano[3,4-c]pyridin-5-oneYield 45.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1,2,3,4-tetrahydro-8-hydroxy-3(phenylmethyl)-5H-[1]benzopyrano[3,4-c]pyridin-5-one (15 g, 0.049 moles), 5-chloro-1-phenyl-1H-tetrazole (9 g, 0.0498 moles), and potassium carbonate (30 g) in dimethylformamide (250 ml) is heated at 85°-95° C. for 5 hours. The reaction mixture is cooled and poured over ice water. The aqueous mixture is allowed to stand at room temperature overnight. The solid is filtered off and washed with water. Recrystallization from ethyl acetate gave the product (10.14 g), mp 165°-166° C.

Workup

  1. temperatureis heated at 85°-95° C. for 5 hours
  2. temperatureThe reaction mixture is cooled
  3. filtrationThe solid is filtered off
  4. washwashed with water
  5. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-d1e81e45b06447a3b7a65cfdc09f68c7
Source dataset
uspto-grants-1983_05
Patent number
US04382939

Reaction notes

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