Lithium hydroxide, monohydrate → 2-Aminocarbonylamino-3-carbamoylindole-6-carboxylic acid

HRID 216638Notes

Reaction equation

HRID 216638 reaction equation
O.[OH-].[Li+].[NH2:4][C:5]([NH:7][C:8]1[NH:9][C:10]2[C:15]([C:16]=1[C:17]([NH2:19])=[O:18])=[CH:14][CH:13]=[C:12]([C:20]([O:22]C)=[O:21])[CH:11]=2)=[O:6]>O1CCCC1.CO.O>[NH2:4][C:5]([NH:7][C:8]1[NH:9][C:10]2[C:15]([C:16]=1[C:17](=[O:18])[NH2:19])=[CH:14][CH:13]=[C:12]([C:20]([OH:22])=[O:21])[CH:11]=2)=[O:6]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 249872232-Aminocarbonylamino-6-methoxycarbonylindole-3-carboxamide2×

Product 1

HCID 591898752-Aminocarbonylamino-3-carbamoylindole-6-carboxylic acidYield 99.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

Lithium hydroxide monohydrate (1.5 g, 36 mmol) was added to a solution mixture of 2-aminocarbonylamino-6-methoxycarbonylindole-3-carboxamide (Compound 2-17, 1.0 g, 3.6 mmol) in tetrahydrofuran, methanol and water (tetrahydrofuran/methanol/water=3/1/1, 50 mL), and the mixture was stirred at 65° C. for 7 hours. After the reaction mixture was concentrated under reduced pressure, 6 N hydrochloric acid (4 mL) was added to the residue under ice-cooling. The precipitated solid was washed with water (20 mL), chloroform (20 mL), and dried under reduced pressure to give the title compound (0.94 g) as a colorless solid (yield 99%).

Workup

  1. concentrationAfter the reaction mixture was concentrated under reduced pressure, 6 N hydrochloric acid (4 mL)
  2. additionwas added to the residue under ice-
  3. temperaturecooling
  4. washThe precipitated solid was washed with water (20 mL), chloroform (20 mL)
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-aecc5ae3fcf04ed0b22eef786df545ad
Source dataset
uspto-grants-2012_06
Patent number
US08193237B2

Reaction notes

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