3-Methylglutaric anhydride → HCID 86729773, compound

HRID 2272616Notes

Reaction equation

HRID 2272616 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][CH3:11])[CH:3]=1.[CH3:12][CH:13]1[CH2:19][C:18](=[O:20])[O:17][C:15](=[O:16])[CH2:14]1>C1COCC1>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([NH:1][C:18](=[O:20])[CH2:19][CH:13]([CH3:12])[CH2:14][C:15]([OH:17])=[O:16])=[CH:3][C:4]=1[O:10][CH3:11])#[N:7]

Participants

4

Reactant 2

HCID 778283-Methylglutaric anhydrideHCID 2327354-Amino-2-methoxybenzonitrile

Product 1

HCID 86729773HCID 86729773, compoundYield 108.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the compound obtained in Step 1 (670 mg, 4.52 mmol) and 3-methylglutaric anhydride (579 mg, 4.52 mmol) in THF (20 mL) was heated with reflux for 14 hr. The reaction solution was concentrated under reduced pressure to give 5-((4-cyano-3-methoxyphenyl)amino)-3-methyl-5-oxopentanoic acid (1.35 g, 4.89 mmol, quantitative) as a brownish-red oil.

Workup

  1. temperaturewith reflux for 14 hr
  2. concentrationThe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-69a25a5498704351ac52767163cbca27
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Reaction notes

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