Hydrochloric Acid → 6-(4-(((5-Fluoro-2-oxoindolin-3-ylidene)hydrazono)methyl)benzamido)hexanoic acid

HRID 251684

Reaction equation

HRID 251684 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10](=[O:31])[C:11]1[CH:16]=[CH:15][C:14]([CH:17]=[N:18][N:19]=[C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([F:29])[CH:27]=3)[NH:22][C:21]2=[O:30])=[CH:13][CH:12]=1.CO.[Li+].[OH-].Cl>O>[F:29][C:26]1[CH:27]=[C:28]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21](=[O:30])[C:20]2=[N:19][N:18]=[CH:17][C:14]1[CH:13]=[CH:12][C:11]([C:10]([NH:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:32])=[O:2])=[O:31])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 1363879766-(4-(((5-Fluoro-2-oxoindolin-3-ylidene)hydrazono)methyl)benzamido)hexanoic acid methyl ester

Product 1

HCID 1363879786-(4-(((5-Fluoro-2-oxoindolin-3-ylidene)hydrazono)methyl)benzamido)hexanoic acidYield 28%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-(4-(((5-fluoro-2-oxoindolin-3-ylidene)hydrazono)methyl)benzamido)hexanoic acid methyl ester (438 mg, 1 mmol) and 300 ml of CH3OH were stirred at room temperature while 25 ml of 4 N solution of LiOH in H2O was added. The mixture was stirred for 24 hours at room temperature. The mixture is neutralized with concentrated hydrochloric acid to pH 7 and evaporated under vacuum to remove methanol. The residue was adjusted to pH 3 with concentrated hydrochloric acid. The solids were collected by vacuum filtration, washed with water and dried under vacuum to give the title compound (119 mg, 28% yield) as a brown solid. LC-MS (m/z) 425 (M+1).

Workup

  1. additionwas added
  2. customevaporated under vacuum
  3. customto remove methanol
  4. filtrationThe solids were collected by vacuum filtration
  5. washwashed with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-a082d07f649a4f71b0a003317c38e9f5
Source dataset
uspto-grants-2011_01
Patent number
US07863315B2

Linked notes

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