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Methyl iodide → 4-cyclopropylmethoxy-N-((S)-6-formyl-1,2,3,4-tetrahydronaphthalen-2-yl)-N-methylbenzamide

HRID 77412
Notes
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Reaction equation

HRID 77412 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:26]=[CH:25][C:9]([C:10]([NH:12][C@H:13]3[CH2:22][CH2:21][C:20]4[C:15](=[CH:16][CH:17]=[C:18]([CH:23]=[O:24])[CH:19]=4)[CH2:14]3)=[O:11])=[CH:8][CH:7]=2)[CH2:3][CH2:2]1.[CH3:27]I.[H-].[Na+].[Cl-].[NH4+]>CN(C=O)C>[CH:1]1([CH2:4][O:5][C:6]2[CH:26]=[CH:25][C:9]([C:10]([N:12]([C@H:13]3[CH2:22][CH2:21][C:20]4[C:15](=[CH:16][CH:17]=[C:18]([CH:23]=[O:24])[CH:19]=4)[CH2:14]3)[CH3:27])=[O:11])=[CH:8][CH:7]=2)[CH2:3][CH2:2]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 867627484-Cyclopropylmethoxy-N-((S)-6-formyl-1,2,3,4-tetrahydronaphthalen-2-yl)benzamide

Product 1

HCID 867627474-cyclopropylmethoxy-N-((S)-6-formyl-1,2,3,4-tetrahydronaphthalen-2-yl)-N-methylbenzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-cyclopropylmethoxy-N—((S)-6-formyl-1,2,3,4-tetrahydronaphthalen-2-yl)-benzamide (2.70 g), methyl iodide (0.534 ml) and DMF (100 ml) was admixed at 0° C. with sodium hydride (55% in paraffin oil; 0.34 g) in portions. After 15 minutes, the reaction mixture was poured into saturated ammonium chloride solution and extracted with ethyl acetate. The organic phase was dried over sodium sulfate and concentrated. The residue was chromatographed on silica gel (eluent: 30% n-heptane in ethyl acetate). The product was thus obtained with the molecular weight of 363.46 (C23H25NO3); MS (ESI): 364 (M+H+).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was chromatographed on silica gel (eluent: 30% n-heptane in ethyl acetate)
  5. customThe product was thus obtained with the molecular weight of 363.46 (C23H25NO3)

Sources & evidence

ORD record
ord-d659b20a3ad64c6dbbd147f48f3c3ecc
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08841290B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes