Sodium Hydroxide → HCID 178433812, compound

HRID 2271446Notes

Reaction equation

HRID 2271446 reaction equation
[OH:1][C:2]1[C:7]([NH:8]/[N:9]=[C:10]2/[C:11]([CH3:26])=[N:12][N:13]([C:16]3[CH:25]=[CH:24][C:23]4[CH2:22][CH2:21][CH2:20][CH2:19][C:18]=4[CH:17]=3)[C:14]/2=[O:15])=[CH:6][CH:5]=[CH:4][C:3]=1[C:27]1[O:31][C:30]([C:32]([OH:34])=[O:33])=[CH:29][CH:28]=1.[OH-].[Na+:36]>O1CCCC1>[Na+:36].[Na+:36].[OH:1][C:2]1[C:7]([NH:8]/[N:9]=[C:10]2/[C:11]([CH3:26])=[N:12][N:13]([C:16]3[CH:25]=[CH:24][C:23]4[CH2:22][CH2:21][CH2:20][CH2:19][C:18]=4[CH:17]=3)[C:14]/2=[O:15])=[CH:6][CH:5]=[CH:4][C:3]=1[C:27]1[O:31][C:30]([C:32]([O-:34])=[O:33])=[CH:29][CH:28]=1.[OH:1][C:2]1[C:7]([NH:8]/[N:9]=[C:10]2/[C:11]([CH3:26])=[N:12][N:13]([C:16]3[CH:25]=[CH:24][C:23]4[CH2:22][CH2:21][CH2:20][CH2:19][C:18]=4[CH:17]=3)[C:14]/2=[O:15])=[CH:6][CH:5]=[CH:4][C:3]=1[C:27]1[O:31][C:30]([C:32]([O-:34])=[O:33])=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178433810HCID 178433810, compound

Product 1

HCID 178433812HCID 178433812, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(Z)-5-(2-hydroxy-3-{N′-[3-methyl-5-oxo-1-(5,6,7,8-tetrahydro-naphthalen-2-yl)-1,5-dihydro-pyrazol-4-ylidene]-hydrazino}-phenyl)-furan-2-carboxylic acid 7d (110 mg, 0.24 mmol) was dissolved in 4 mL of tetrahydrofuran to form a dark red suspension. The reaction mixture was added dropwise with 1 M sodium hydroxide solution (0.4 mL, 0.44 mmol), stirred for 2 hours at room temperature. The reaction mixture was filtered, then the filtrate was added with 4 mL methanol and concentrated under reduced pressure. The resulting solid was washed with hexane to obtain the title compound (Z)-5-(2-hydroxy-3-{N′-[3-methyl-5-oxo-1-(5,6,7,8-tetrahydro-naphthalen-2-yl)-1,5-dihydro-pyrazol-4-ylidene]-hydrazino}-phenyl)-furan-2-carboxylic acid disodium salt 14 (115 mg, yield: 81.8%) as a dark solid.

Workup

  1. customto form a dark red suspension
  2. filtrationThe reaction mixture was filtered
  3. additionthe filtrate was added with 4 mL methanol
  4. concentrationconcentrated under reduced pressure
  5. washThe resulting solid was washed with hexane

Sources & evidence

ORD record
ord-e7309c4a8abd4656872dc64103d7a5ac
Source dataset
uspto-grants-2015_09
Patent number
US09120762B2

Reaction notes

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