Methanol → HCID 178433814, compound

HRID 238710

Reaction equation

HRID 238710 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-].[OH:36][CH2:37][CH2:38][N+:39]([CH3:42])([CH3:41])[CH3:40].CO>O1CCCC1>[OH:36][CH2:37][CH2:38][N+:39]([CH3:42])([CH3:41])[CH3:40].[OH:36][CH2:37][CH2:38][N+:39]([CH3:42])([CH3:41])[CH3:40].[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

Participants

5

Reactant 3

HCID 887MethanolHCID 31255Choline, hydroxideHCID 178433810HCID 178433810, compound

Product 1

HCID 178433814HCID 178433814, compoundYield 96.6%

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 (100 mg, 0.22 mmol) was dissolved in 5 mL of tetrahydrofuran to form a dark red suspension. The reaction mixture was added with 45% solution of choline hydroxide in methanol (45 mg, 0.44 mmol) to form a purple solution, and stirred for 1 hour at room temperature. The solid was precipitated from solution, filtered, then the filter cake was washed with tetrahydrofuran (1 mL×3) and dired in vacuo 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 bis-(choline) 8 (140 mg, yield: 96.6%) as a dark red solid.

Workup

  1. customto form a dark red suspension
  2. customto form a purple solution
  3. customThe solid was precipitated from solution
  4. filtrationfiltered
  5. washthe filter cake was washed with tetrahydrofuran (1 mL×3) and dired in vacuo

Sources & evidence

ORD record
ord-77d9cb3cff654ae5ac5b38aca064cdc7
Source dataset
uspto-grants-2014_02
Patent number
US08642637B2

Linked notes

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