Indoline → HCID 22247323, compound

HRID 1531994Notes

Reaction equation

HRID 1531994 reaction equation
N1C2C(=CC=CC=2)CC1.[CH2:10]([N:18]1[C:26]2[C:21](=[CH:22][C:23]([C:35]([O:37]C)=[O:36])=[C:24]([CH3:34])[C:25]=2[NH:27][C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:20][CH2:19]1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[OH-].[Na+]>CO.O>[CH2:10]([N:18]1[C:26]2[C:21](=[CH:22][C:23]([C:35]([OH:37])=[O:36])=[C:24]([CH3:34])[C:25]=2[NH:27][C:28](=[O:33])[C:29]([CH3:30])([CH3:31])[CH3:32])[CH2:20][CH2:19]1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 3

HCID 10328IndolineHCID 14798Sodium HydroxideHCID 22247353HCID 22247353, compound

Product 1

HCID 22247323HCID 22247323, compoundYield 67.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

0.87 (3H, br-t, J=7 Hz, —(CH2)7CH3), 1.00-1.70 (12H, m, —CH2(CH2)6—), 1.34 (9H, s, —C(CH3)3), 2.39 (3H, s, indoline C6—CH3), 2.93 (2H, t, J=8 Hz, indoline C3—H2), 3.25 (2H, t, J=7 Hz, >NCH2—), 3.51 (2H, t, J=8 Hz, indoline C2—H2), 3.79 (3H, s, —CO2 CH3), 6.76 (1H, br, —CONH—), 7.55 (1H, s, indoline Ce—H). (6) N-(1-Octyl-5-methoxycarbonyl-6-methylindolin-7-yl)-2,2-dimethylpropanamide (580 mg) was dissolved in methanol (10 ml) and a solution of NaOH (290 mg) in water (5 ml) was added, which was followed by stirring at 60° C. for 4 hr. Methanol was evaporated under reduced pressure. Water (50 ml) was added to the residue and the mixture was washed with ethyl acetate (20 ml). The aqueous layer was adjusted to pH 6-7 with 2N sulfuric acid and extracted with chloroform (100 ml). The chloroform layer was washed with water and dried over anhydrous sodium. sulfate. Chloroform was evaporated under reduced pressure to give 380 mg of the title compound.

Workup

  1. customMethanol was evaporated under reduced pressure
  2. additionWater (50 ml) was added to the residue
  3. washthe mixture was washed with ethyl acetate (20 ml)
  4. extractionextracted with chloroform (100 ml)
  5. washThe chloroform layer was washed with water
  6. dry with materialdried over anhydrous sodium
  7. customChloroform was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c91ecbdcd38a42b7a69a1de22111e49c
Source dataset
uspto-grants-2001_03
Patent number
US06200988B1

Reaction notes

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