3-Aminophenol → HCID 178426948, compound

HRID 2352850Notes

Reaction equation

HRID 2352850 reaction equation
O[CH:2]=[C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([C:14]3[CH:15]=[C:16]([NH:20][C:21]([C:23]4[N:24]([CH3:29])[N:25]=[C:26]([CH3:28])[CH:27]=4)=[O:22])[CH:17]=[CH:18][CH:19]=3)=[O:13])=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:30].[NH2:31][C:32]1[CH:33]=[C:34]([OH:38])[CH:35]=[CH:36][CH:37]=1>C1COCC1>[OH:38][C:34]1[CH:33]=[C:32]([NH:31][CH:2]=[C:3]2[C:11]3[C:6](=[CH:7][C:8]([C:12]([C:14]4[CH:15]=[C:16]([NH:20][C:21]([C:23]5[N:24]([CH3:29])[N:25]=[C:26]([CH3:28])[CH:27]=5)=[O:22])[CH:17]=[CH:18][CH:19]=4)=[O:13])=[CH:9][CH:10]=3)[NH:5][C:4]2=[O:30])[CH:37]=[CH:36][CH:35]=1

Participants

4

Reactant 2

HCID 115683-AminophenolHCID 178426964HCID 178426964, compound

Product 1

HCID 178426948HCID 178426948, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

A small screw cap test tube was charged with 2,5-Dimethyl-2H-pyrazole-3-carboxylic acid [3-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (as prepared in Example 60, 120 mg, 0.298 mmol) and THF (2 mL). To the resulting solution was added 3-aminophenol (40 mg, 0.3665 mmol), and the mixture was stirred for 24 h at 65° C. Subsequently, the reaction mixture was cooled to room temperature and concentrated in vacuo. The solid residue was recrystallized with ˜5 mL of i-prOH affording the title compound in 70% yield (0.103 g, 0.2087 mmol).

Workup

  1. customA small screw cap test tube
  2. temperatureSubsequently, the reaction mixture was cooled to room temperature
  3. concentrationconcentrated in vacuo
  4. customThe solid residue was recrystallized with ˜5 mL

Sources & evidence

ORD record
ord-34fc3aed73de4319af7f0da306e16941
Source dataset
uspto-grants-2010_07
Patent number
US07749530B2

Reaction notes

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