Sodium Hydroxide → (2-Amino-5-(prop-2-yn-1-yloxy)phenyl)(4-isopropylphenyl)methanone

HRID 1046353Notes

Reaction equation

HRID 1046353 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:12]2[CH:17]=[C:16]([O:18][CH2:19][C:20]#[CH:21])[CH:15]=[CH:14][C:13]=2[N+:22]([O-])=O)=[O:11])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[OH-].[Na+]>C(O)(=O)C.[Fe]>[NH2:22][C:13]1[CH:14]=[CH:15][C:16]([O:18][CH2:19][C:20]#[CH:21])=[CH:17][C:12]=1[C:10]([C:7]1[CH:6]=[CH:5][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:9][CH:8]=1)=[O:11]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 45480510(4-Isopropylphenyl)(2-nitro-5-(prop-2-yn-1-yloxy)phenyl)methanone

Product 1

HCID 45139628(2-Amino-5-(prop-2-yn-1-yloxy)phenyl)(4-isopropylphenyl)methanone

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 10.59 g (30.7 mmol) (4-isopropyl-phenyl)-(2-nitro-5-propargyloxy-phenyl)-methanone in 250 ml acetic acid are added 13.6 g (246 mmol) iron powder. After stirring for 20 h at rt the reaction mixture is basified by the addition of 2M sodium hydroxide solution, filtered and extracted with dichloromethane. Aider purification by chromatography using hexanes/ethyl acetate (7:3) as eluent (2-amino-5-propargyloxy-phenyl)-(4-isopropyl-phenyl)-methanone is obtained.

Workup

  1. filtrationfiltered
  2. extractionextracted with dichloromethane
  3. customAider purification by chromatography
  4. customis obtained

Sources & evidence

ORD record
ord-8ba1631043804390acaa5767f5924e78
Source dataset
uspto-grants-2013_10
Patent number
US08569317B2

Reaction notes

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