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

HRID 589350Notes

Reaction equation

HRID 589350 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([NH:13][C:14]1[CH:35]=[CH:34][C:17]([CH2:18][C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]([CH2:28][C:29]([O:31]CC)=[O:30])[N:20]=2)=[CH:16][CH:15]=1)=[O:12].O.[OH-].[Li+].O.Cl>O1CCCC1.CO>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([NH:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:18][C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]([CH2:28][C:29]([OH:31])=[O:30])[N:20]=2)=[CH:34][CH:35]=1)=[O:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 89590254ethyl 2-[3-[4-(2-naphthamido)benzyl]-1H-indazol-1-yl]acetate

Product 1

HCID 715717122-[3-[4-(2-naphthamido)benzyl]-1H-indazol-1-yl]acetic acidYield 87.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

575 mg (1.24 mmol) ethyl 2-[3-[4-(2-naphthamido)benzyl]-1H-indazol-1-yl]acetate was dissolved in a mixed solution of 10 mL tetrahydrofuran and 3 mL methanol, in an ice bath 10 mL aqueous solution dissolving 333 mg (7.93 mmol) lithium hydroxide monohydrate 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, the pH value was adjusted to be acidic with diluted hydrochloric acid. A solid precipitated, it was filtered, dried to obtain a white solid 470 mg (1.08 mmol), at a yield of 87.1%.

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-ff4b8d8452c047579d0a86fd4d0fdcbc
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

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