Methanol → HCID 23153952, compound

HRID 1175790Notes

Reaction equation

HRID 1175790 reaction equation
[CH:1]([O:4][C:5]1[C:14]([O:15][CH3:16])=[CH:13][C:8]([C:9]([O:11]C)=[O:10])=[C:7]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[CH:6]=1)([CH3:3])[CH3:2].CO.[OH-].[Na+]>O1CCCC1>[CH:1]([O:4][C:5]1[C:14]([O:15][CH3:16])=[CH:13][C:8]([C:9]([OH:11])=[O:10])=[C:7]([NH:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=2)[CH:6]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 23153963HCID 23153963, compound

Product 1

HCID 23153952HCID 23153952, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 4-isopropoxy-5-methoxy-2-(4-methoxybenzyl)aminobenzoate (18.9 g), methanol (50 ml), tetrahydrofuran (150 ml) and a 1N aqueous sodium hydroxide solution (80 ml) was stirred at room temperature for 1 night, heated under reflux for 12 hours. The solvent was distilled off under reduced pressure, the reaction mixture was adjusted to about pH 6 by adding 1N hydrochloric acid and 5% citric acid. The precipitated solid was collected by filtration, washed and dried to obtain the target compound (18.0 g).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 12 hours
  3. distillationThe solvent was distilled off under reduced pressure
  4. additionby adding 1N hydrochloric acid and 5% citric acid
  5. filtrationThe precipitated solid was collected by filtration
  6. washwashed
  7. customdried

Sources & evidence

ORD record
ord-be05615053164a6eadc4adca6121fe9d
Source dataset
uspto-grants-2010_11
Patent number
US07842701B2

Reaction notes

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