Hydrochloric Acid → HCID 18937727, compound

HRID 357653Notes

Reaction equation

HRID 357653 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:35]=[CH:34][C:8]([CH2:9][N:10]2[C:14]([C:15]([O:17]CC)=[O:16])=[C:13]([C:20](=[O:33])[C:21]3[CH:26]=[C:25]([O:27][CH3:28])[C:24]([CH3:29])=[CH:23][C:22]=3[N+:30]([O-:32])=[O:31])[N:12]=[N:11]2)=[CH:7][CH:6]=1.Cl>O1CCCC1.CCOCC.O>[CH3:3][O:4][C:5]1[CH:35]=[CH:34][C:8]([CH2:9][N:10]2[C:14]([C:15]([OH:17])=[O:16])=[C:13]([C:20](=[O:33])[C:21]3[CH:26]=[C:25]([O:27][CH3:28])[C:24]([CH3:29])=[CH:23][C:22]=3[N+:30]([O-:32])=[O:31])[N:12]=[N:11]2)=[CH:7][CH:6]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18937589HCID 18937589, compound

Product 1

HCID 18937727HCID 18937727, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 1N aqueous sodium hydroxide solution (1.1 ml) was added to a solution of ethyl 1-(4-methoxybenzyl)-4-(5-methoxy-4-methyl-2-nitrobenzoyl )-1,2,3-triazole-5-carboxylate (b-1) (243 mg, 0.535 mmole) obtained in the preceding step (b) in tetrahydrofuran (6 ml), and the mixture was stirred at room temperature for 4 hours. The reaction mixture was diluted with ether, and water was added. The aqueous layer was acidified with hydrochloric acid, it was extracted with ethyl acetate, and washed with water and a saturated aqueous saline. After the organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to give 1-(4-methoxybenzyl)-4-(5-methoxy-4-methyl-2-nitrobenzoyl)-1,2, 3-triazole-5-carboxylic acid (c-1': LP) as a pale yellow crystalline powder (204 mg, 89%). Next, 1-(4-methoxybenzyl)-4-(5-methoxy-4-methyl-2-nitrobenzoyl)-1,2,3-triazole-5-carboxylic acid (c-1': LP) (200 mg, 0.469 mmole) thus obtained was dissolved in a mixed solvent of ethanol (12 ml) and ethyl acetate (12 ml), 10% palladium on carbon (25 mg) was added, and the mixture was stirred under the hydrogen atmosphere at room temperature for 6.5 hours. After the reaction mixture was filtered through celite, the filtrate was concentrated under reduced pressure, and precipitates were collected by filtration to give 4-(2-amino-5-methoxy-4-methylbenzoyl)-1-(4-methoxybenzyl)-1,2,3-triazole-5-carboxylic acid (c-1 LP) as a red crystalline powder (178 mg, 96%).

Workup

  1. additionwas added
  2. extractionwas extracted with ethyl acetate
  3. washwashed with water
  4. dry with materialAfter the organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-1b555fd60a0c419da50c1c7bf247484b
Source dataset
uspto-grants-1998_11
Patent number
US05840895

Reaction notes

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