Hydrochloric Acid → 2-[3-[4-(4-chlorobenzamido)benzyl]-1H-indazol-1-yl]acetic acid

HRID 589360Notes

Reaction equation

HRID 589360 reaction equation
[Cl:1][C:2]1[CH:32]=[CH:31][C:5]([C:6]([NH:8][C:9]2[CH:30]=[CH:29][C:12]([CH2:13][C:14]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[N:16]([CH2:23][C:24]([O:26]CC)=[O:25])[N:15]=3)=[CH:11][CH:10]=2)=[O:7])=[CH:4][CH:3]=1.CO.O.[OH-].[Li+].Cl>O1CCCC1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:8][C:9]2[CH:30]=[CH:29][C:12]([CH2:13][C:14]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[N:16]([CH2:23][C:24]([OH:26])=[O:25])[N:15]=3)=[CH:11][CH:10]=2)=[O:7])=[CH:31][CH:32]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 89590282ethyl 2-[3-[4-(4-chlorobenzamido)benzyl]-1H-indazol-1-yl]acetate

Product 1

HCID 715718292-[3-[4-(4-chlorobenzamido)benzyl]-1H-indazol-1-yl]acetic acidYield 74.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-[3-[4-(4-chlorobenzamido)benzyl]-1H-indazol-1-yl]acetate (100 mg, 0.223 mmol) was dissolved in 3 mL tetrahydrofuran, and 1 mL methanol, 3 mL water were added. In an ice bath was, 47 mg (1.12 mmol) lithium hydroxide monohydrate was added. I was moved to be at room temperature and reacted for 10 minutes. The reaction was monitored to be complete by TLC. Diluted hydrochloric acid was added to adjust pH to be acidic. Water was added, pumping filtered, dried to obtain a white solid 70 mg, at a yield of 74.9%

Workup

  1. customIn an ice bath was
  2. customto be at room temperature
  3. customreacted for 10 minutes
  4. filtrationpumping filtered
  5. customdried

Sources & evidence

ORD record
ord-c24f70785ba045d1acc62f7efbece5b4
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

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