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

HRID 251692Notes

Reaction equation

HRID 251692 reaction equation
C[O:2][C:3](=[O:30])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10](=[O:29])[C:11]1[CH:16]=[CH:15][C:14]([CH:17]=[C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([F:27])[CH:25]=3)[NH:20][C:19]2=[O:28])=[CH:13][CH:12]=1.CO.[Li+].[OH-].Cl>O>[F:27][C:24]1[CH:25]=[C:26]2[C:21](=[CH:22][CH:23]=1)[NH:20][C:19](=[O:28])[C:18]2=[CH:17][C:14]1[CH:15]=[CH:16][C:11]([C:10]([NH:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:30])=[O:2])=[O:29])=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 690323706-(4-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)benzamido)hexanoic acid methyl ester

Product 1

HCID 690327486-(4-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)benzamido)hexanoic acidYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-(4-((5-fluoro-2-oxoindolin-3-ylidene)methyl)benzamido)hexanoic acid methyl ester (410 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 (305 mg, 77% yield) as a brown solid. LC-MS (m/z) 397 (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-480b87e2fc8d4157a40a7f373e1654b0
Source dataset
uspto-grants-2011_01
Patent number
US07863315B2

Reaction notes

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