Methyl 3-{[[2-(diethylamino)ethyl](methyl)amino]methyl}-5-methylbenzoate → 3-{[[2-(Diethylamino)ethyl](methyl)amino]methyl}-5-methylbenzoic Acid

HRID 14129

Reaction equation

HRID 14129 reaction equation
[CH2:1]([N:3]([CH2:20][CH3:21])[CH2:4][CH2:5][N:6]([CH2:8][C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([CH3:19])[CH:18]=1)[C:12]([O:14]C)=[O:13])[CH3:7])[CH3:2]>CO.O1CCCC1>[CH2:20]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][N:6]([CH2:8][C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([CH3:19])[CH:18]=1)[C:12]([OH:14])=[O:13])[CH3:7])[CH3:21]

Participants

3

Reactant 1

HCID 21086144Methyl 3-{[[2-(diethylamino)ethyl](methyl)amino]methyl}-5-methylbenzoate

Product 1

HCID 210856653-{[[2-(Diethylamino)ethyl](methyl)amino]methyl}-5-methylbenzoic Acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A mixture of methyl 3-{[[2-(diethylamino)ethyl](methyl)amino]methyl}-5-methylbenzoate (296 mg, 1.01 mmol) and 3:1:1 methanol/tetrahydrofuran/2 N sodium hydroxide (10 mL) is stirred overnight and then partitioned between ethyl acetate and water. The aqueous layer is acidified to pH 3 with 1 N hydrochloric acid and extracted with chloroform. The aqueous layer is concentrated under reduced pressure to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ 7.99 (s, 1H), 7.82 (s, 1H), 7.80 (s, 1H), 4.56 (m, 2H), 4.31 (m, 2H), 3.98 (m, 2H), 3.17 (m, 4H), 2.51 (s, 3H), 2.50 (s, 3H), 1.27 (m, 6H).

Workup

  1. custompartitioned between ethyl acetate and water
  2. extractionextracted with chloroform
  3. concentrationThe aqueous layer is concentrated under reduced pressure

Sources & evidence

ORD record
ord-c4427cce21244c118cd0a6bd9bb56707
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Linked notes

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