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

HRID 589367Notes

Reaction equation

HRID 589367 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][N:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C: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>[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][N:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]([CH2:28][C:29]([OH:31])=[O:30])=[N:20]2)=[CH:34][CH:35]=1)=[O:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 90449170ethyl 2-[1-[4-(2-naphthamido)benzyl]-1H-indazol-3-yl]acetate

Product 1

HCID 715568942-[1-[4-(2-naphthamido)benzyl]-1H-indazol-3-yl]acetic acidYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-[1-[4-(2-naphthamido)benzyl]-1H-indazol-3-yl]acetate (226 mg, 0.488 mmol) was dissolved in tetrahydrofuran (10 mL), and in an ice bath 10 mL aqueous solution of lithium hydroxide monohydrate (62 mg, 1.48 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 123 mg, at a yield of 58%.

Workup

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

Sources & evidence

ORD record
ord-d18a1ceefe2849e8b030f2d3b8184a59
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

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