Water → HCID 4649610, compound

HRID 2272608Notes

Reaction equation

HRID 2272608 reaction equation
[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([NH2:16])=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2].[CH3:17][CH:18]1[CH2:24][C:23](=[O:25])[O:22][C:20](=[O:21])[CH2:19]1.O>C1COCC1>[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([NH:16][C:23](=[O:25])[CH2:24][CH:18]([CH3:17])[CH2:19][C:20]([OH:22])=[O:21])=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 85883-Amino-9-ethylcarbazoleHCID 778283-Methylglutaric anhydride

Product 1

HCID 4649610HCID 4649610, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 9-ethyl-9H-carbazol-3-amine (4.21 g, 20 mmol) in THF (40 mL) was added 3-methylglutaric anhydride (2.56 g, 20.00 mmol), and the mixture was stirred at 90° C. for 4 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried, and the solvent was evaporated under reduced pressure to give 5-(9-ethyl-9H-carbazol-3-ylamino)-3-methyl-5-oxopentanoic acid (6.23 g, 18.41 mmol, 92%) as a white powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-2d03cd461cad4930adb2798a5721d718
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Reaction notes

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