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

HRID 2216928Notes

Reaction equation

HRID 2216928 reaction equation
[CH3:1][O:2][C:3]([N:5]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][C:13](O)=[O:14])=[O:4].[CH3:22]O>>[CH3:1][O:2][C:3]([N:5]1[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:13]([O:14][CH3:22])=[CH:12][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]1=2)=[O:4]

Participants

3

Reactant 2

HCID 887MethanolHCID 11219868[2-(Methoxycarbonyl-phenyl-amino)-phenyl]-acetic acid

Product 1

HCID 11208289Methyl 10-methoxy-5H-dibenz[b,f]azepine-5-carboxylateYield 80%

Conditions

Temperature
100 °C

Procedure

A mixture of [2-(methoxycarbonyl-phenyl-amino)-phenyl]-acetic acid (16 g, 55.5 mmol) and polyphosphoric acid (29 g, 167 mmol in terms of P2O5) is heated to 100° C. for 4 hours. To the reaction mixture, methanol (50 ml) is added dropwise at 65° C. with stirring. The resulting suspension is cooled to room temperature, filtered and washed with methanol (40 ml). The white crystals are dried to yield 12.2 g of pure title compound (80%).

Workup

  1. temperatureThe resulting suspension is cooled to room temperature
  2. filtrationfiltered
  3. washwashed with methanol (40 ml)
  4. customThe white crystals are dried

Sources & evidence

ORD record
ord-2738b4c197734ee49e3b471bc8fbd3c4
Source dataset
uspto-grants-2006_09
Patent number
US07112673B2

Reaction notes

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