Succinic anhydride → 4-[[4-[(2-Methoxyethoxy)methoxy]phenyl]amino]-4-oxobutanoic acid

HRID 1603242Notes

Reaction equation

HRID 1603242 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=1.[C:15]1(=[O:21])[O:20][C:18](=[O:19])[CH2:17][CH2:16]1>ClCCl.N1C=CC=CC=1.CO>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([NH:14][C:15](=[O:21])[CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[CH:12][CH:13]=1

Participants

6

Reactant 2

HCID 7922Succinic anhydrideHCID 131356894-[(2-Methoxyethoxy)methoxy]aniline

Product 1

HCID 196090764-[[4-[(2-Methoxyethoxy)methoxy]phenyl]amino]-4-oxobutanoic acidYield 55%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 510 mg (2.58 mmol) of 4-[(2-methoxyethoxy) methoxy]benzenamine (22) in 8 mL of dichloromethane and 2 mL of anhydrous pyridine (Aldrich) was added 380 mg (3.8 mmol) of succinic anhydride portionwise. The mixture was stirred at room temperature for 18 hours. To the reaction mixture was added 20 mL of methanol and the mixture was stirred at room temperature for 2 hours. The mixture was concentrated and purified by preparative thin layer chromatography using 8:2 chloroform:methanol as an eluent to yield 420 mg (1.41 mmol, 55%) of 4-[[4-[(2-methoxyethoxy)methoxy]phenyl]amino]-4-oxobutanoic acid (23). NMR, IR and MS data confirmed the compound identity.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. concentrationThe mixture was concentrated
  3. custompurified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-e37b7dd84098450aaf28a32dee369281
Source dataset
uspto-grants-1999_11
Patent number
US05986094

Reaction notes

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