3-Methyl-2-butanone → 2,3,3-Trimethyl-4,6-dicarboxy-3H-indole

HRID 61513

Reaction equation

HRID 61513 reaction equation
[NH:1]([C:3]1[CH:4]=[C:5]([C:12]([OH:14])=[O:13])[CH:6]=[C:7]([C:9]([OH:11])=[O:10])[CH:8]=1)N.[CH:15]([C:18]([CH3:20])=O)([CH3:17])[CH3:16]>C(O)(=O)C>[CH3:20][C:18]1[C:15]([CH3:17])([CH3:16])[C:4]2[C:3](=[CH:8][C:7]([C:9]([OH:11])=[O:10])=[CH:6][C:5]=2[C:12]([OH:14])=[O:13])[N:1]=1

Participants

4

Reactant 2

HCID 112513-Methyl-2-butanoneHCID 27723645-Hydrazinylbenzene-1,3-dicarboxylic acid

Product 1

HCID 666034172,3,3-Trimethyl-4,6-dicarboxy-3H-indoleYield 95.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 5-hydrazinylbenzene-1,3-dicarboxylic acid (30.0 g, 129 mmol), isopropylmethylketone (22.0 mL, 205 mmol) in acetic acid (300 mL) and was heated under reflux in an oil bath for 18 h. After cooling to ambient temperature the solvent was evaporated off under reduced pressure to a small volume of ˜100 mL. To the crude mixture was added iPrOH (200 mL) and the solid was collected with a filter funnel, washed with EtOAc (3×200 mL) and ethyl ether (2×200 mL) and dried. Further drying of the solid in an oven at 50° C. under high vacuum for 18 h provided 30.44 g (95.5%) of the product.

Workup

  1. temperatureunder reflux in an oil bath for 18 h
  2. customwas evaporated off under reduced pressure to a small volume of ˜100 mL
  3. additionTo the crude mixture was added iPrOH (200 mL)
  4. customthe solid was collected with a filter funnel
  5. washwashed with EtOAc (3×200 mL) and ethyl ether (2×200 mL)
  6. customdried
  7. customFurther drying of the solid in an oven at 50° C. under high vacuum for 18 h

Sources & evidence

ORD record
ord-8274997e6bfa423e9c35a065c31f784c
Source dataset
uspto-grants-2016_09
Patent number
US09441270B2

Linked notes

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