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

HRID 589370Notes

Reaction equation

HRID 589370 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][N:14]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[C: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.O.[OH-].[Li+].O.Cl>O1CCCC1>[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][N:14]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[C: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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 89590262ethyl 2-[1-[4-(4-chlorobenzamido)benzyl]-1H-indazol-3-yl]acetate

Product 1

HCID 715718312-[1-[4-(4-chlorobenzamido)benzyl]-1H-indazol-3-yl]acetic acidYield 96.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-[1-[4-(4-chlorobenzamido)benzyl]-1H-indazol-3-yl]acetate (159 mg, 0.355 mmol) was dissolved in tetrahydrofuran (10 mL). In an ice bath, 10 mL aqueous solution dissolving lithium hydroxide monohydrate (42 mg, 1.0 mmol) was added. It was reacted at room temperature for 3 h, and the reaction was monitored to be complete by TLC. Water was added into the system, and adjusted to pH≈3-4 with diluted hydrochloric acid. A solid precipitated. It was filtered, and dried to obtain a white solid 144 mg, at a yield of 96.6%.

Workup

  1. additionwas added
  2. customIt was reacted at room temperature for 3 h
  3. customA solid precipitated
  4. filtrationIt was filtered
  5. customdried

Sources & evidence

ORD record
ord-297ae7fac4ff4159adb7787b56d196dd
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

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