Succinic anhydride → HCID 178525507, compound

HRID 2103937Notes

Reaction equation

HRID 2103937 reaction equation
[O:1]1[C:5](=[O:6])[N:4]=[C:3]([C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=2)[NH:2]1.[C:14]1(=[O:20])[O:19][C:17](=[O:18])[CH2:16][CH2:15]1>N1C=CC=CC=1>[O:1]1[C:5](=[O:6])[N:4]=[C:3]([C:7]2[CH:13]=[CH:12][C:10]([NH:11][C:14](=[O:20])[CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:9][CH:8]=2)[NH:2]1

Participants

4

Reactant 2

HCID 7922Succinic anhydrideHCID 178507458HCID 178507458, compound

Product 1

HCID 178525507HCID 178525507, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

Aniline derivative 16 (0.89 g, 5.0 mmol) was dissolved in pyridine (25 mL). Succinic anhydride (0.75 g, 7.5 mmol) was added together with 4-N,N,-dimethylaminopyridine (63 mg, 0.5 mmol) and the mixture was stirred overnight at 100° C. The solution was concentrated under reduced pressure and the pale brown solid was recrystallized from a mixture of EtOH/MeOH/H2O (60 mL, 5/35/1, v/v/v). After filtration, the mother liquid was concentrated to ˜10 mL to give carboxylic acid 17 as a solid which was dried under vacuum at 50° C. for 16 h. Yield 1.28 g (92%). Rf 0.3 (DCM/MeOH/AcOH, 100/10/1, v/v/v).

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. customthe pale brown solid was recrystallized from a mixture of EtOH/MeOH/H2O (60 mL, 5/35/1, v/v/v)
  3. filtrationAfter filtration
  4. concentrationthe mother liquid was concentrated to ˜10 mL

Sources & evidence

ORD record
ord-3e2e64c032354a4f8e7b82bbbe23441c
Source dataset
uspto-grants-2009_08
Patent number
US07576071B2

Reaction notes

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