Trimethyl orthoformate → Methyl 10-methoxy-5H-dibenz[b,f]azepine-5-carboxylate

HRID 2216926Notes

Reaction equation

HRID 2216926 reaction equation
[CH3:1][O:2][C:3]([N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:9](=[O:16])[CH2:8][C:7]2[CH:17]=[CH:18][CH:19]=[CH:20][C:6]1=2)=[O:4].[CH:21](OC)(OC)OC>CO.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:1][O:2][C:3]([N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:9]([O:16][CH3:21])=[CH:8][C:7]2[CH:17]=[CH:18][CH:19]=[CH:20][C:6]1=2)=[O:4]

Participants

5

Reactant 2

HCID 9005Trimethyl orthoformateHCID 11346171HCID 11346171, compound

Product 1

HCID 11208289Methyl 10-methoxy-5H-dibenz[b,f]azepine-5-carboxylateYield 98.4%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 10-oxo-10,11-dihydro-dibenzo[b,f]azepine-5-carboxylic acid methyl ester (15 g, 56 mmol) in methanol (75 ml) is heated to 60° C. and a catalytic amount of p-toluene sulfonic acid (0.213 g, 1.1 mmol) is added. After addition of trimethyl ortho-formate (6.25 g, 58.9 mmol) the solution is stirred at 60–70° C. for 4 hours. During this reaction the product precipitates as white crystals. The mixture is cooled to room temperature, filtered and dried to yield 15.5 g of pure title compound (98%).

Workup

  1. customDuring this reaction the product
  2. customprecipitates as white crystals
  3. temperatureThe mixture is cooled to room temperature
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-f8483d1ab42b487c926effb172eaf081
Source dataset
uspto-grants-2006_09
Patent number
US07112673B2

Reaction notes

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