Sodium Hydroxide → HCID 20098354, compound

HRID 1768980Notes

Reaction equation

HRID 1768980 reaction equation
[CH3:1][C:2]([NH:5][CH2:6][CH:7]([OH:29])[CH2:8][O:9][C:10]1[CH:28]=[CH:27][CH:26]=[CH:25][C:11]=1[C:12]([NH:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:16]=1[C:17](Cl)=[CH:18][NH:19]2)=[O:13])([CH3:4])[CH3:3].[OH-:30].[Na+]>C(O)C.Cl.O>[CH3:1][C:2]([NH:5][CH2:6][CH:7]([OH:29])[CH2:8][O:9][C:10]1[CH:28]=[CH:27][CH:26]=[CH:25][C:11]=1[C:12]([NH:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:16]=1[CH2:17][C:18](=[O:30])[NH:19]2)=[O:13])([CH3:4])[CH3:3]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 67781931HCID 67781931, compound

Product 1

HCID 20098354HCID 20098354, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2.5 g of the product of Step A in 35 ml of ethanol and 70 ml of 1N hydrochloric acid was refluxed for 1 hour and the reaction mixture was diluted with water, alkalinized with sodium hydroxide and extracted with ethyl acetate. After elimination of the solvent under reduced pressure, 2.5 g of crude product were obtained with crystallized spontaneously from a mixture of solvents: chloroform-ethyl acetate-triethylamine (6-3-1) to obtain 1.9 g of 2-[3[(1,1-dimethylethyl)amino]-2-hydroxypropoxy]-N-[2,3-dihydro-2-oxo-1H-indol-4-yl]benzamide melting at 160° C.

Workup

  1. extractionextracted with ethyl acetate
  2. customAfter elimination of the solvent under reduced pressure, 2.5 g of crude product were obtained
  3. customwith crystallized spontaneously from a mixture of solvents

Sources & evidence

ORD record
ord-fa4d25cc803642bc8571ff0b90f3cf85
Source dataset
uspto-grants-1995_01
Patent number
US05380722

Reaction notes

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