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Toluene → hydroxy-(4-methoxy-phenyl)-acetic acid N'-(3-methoxy-4-prop-2-ynyloxy-benzyl)-hydrazide

HRID 458252
Notes
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Reaction equation

HRID 458252 reaction equation
[CH2:1](Br)[C:2]#[CH:3].C1(C)C=CC=CC=1.[OH:12][C:13]1[CH:33]=[CH:32][C:16]([CH2:17][NH:18][NH:19][C:20](=[O:31])[CH:21]([OH:30])[C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)=[CH:15][C:14]=1[O:34][CH3:35].[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[CH3:35][O:34][C:14]1[CH:15]=[C:16]([CH:32]=[CH:33][C:13]=1[O:12][CH2:3][C:2]#[CH:1])[CH2:17][NH:18][NH:19][C:20](=[O:31])[CH:21]([OH:30])[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 1140TolueneHCID 7842Propargyl bromideHCID 14798Sodium HydroxideHCID 58679590hydroxy-(4-methoxy-phenyl)-acetic acid N'-(4-hydroxy-3-methoxy-benzyl)-hydrazide

Product 1

HCID 58679589hydroxy-(4-methoxy-phenyl)-acetic acid N'-(3-methoxy-4-prop-2-ynyloxy-benzyl)-hydrazide

Reagents, catalysts & solvents 2

HCID 74236
Tetrabutylammonium Bromide
Catalyst
HCID 6344DichloromethaneSolvent

Procedure

A 80% propargyl bromide solution in toluene (2.1 g, 14.5 mmol) is added slowly at room temperature to a mixture of hydroxy-(4-methoxy-phenyl)-acetic acid N′-(4-hydroxy-3-methoxy-benzyl)-hydrazide (4.0 g, 12 mmol), 30% sodium hydroxide solution (3.5 ml, 14.5 mmol) and catalytic amounts of tetrabutylammonium bromide in 35 ml of dichloromethane. The reaction is stirred for 16 hours at +40° C. Subsequently the mixture is evaporated and the residue is diluted with water and dichloromethane. The phases are separated and the aqueous phase is extracted three times with dichloromethane. The combined organic phase is washed with brine, dried over sodium sulfate and evaporated. The remaining oil is purified by chromatography on silica gel (ethyl acetate/hexane 7:3) to obtain hydroxy-(4-methoxy-phenyl)-acetic acid N′-(3-methoxy-4-prop-2-ynyloxy-benzyl)-hydrazide.

Workup

  1. customSubsequently the mixture is evaporated
  2. additionthe residue is diluted with water and dichloromethane
  3. customThe phases are separated
  4. extractionthe aqueous phase is extracted three times with dichloromethane
  5. washThe combined organic phase is washed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customThe remaining oil is purified by chromatography on silica gel (ethyl acetate/hexane 7:3)

Sources & evidence

ORD record
ord-9e256c02d2e9458e958140023de1575f
Source dataset
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07189873B2

Reaction notes

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