Sodium Hydroxide → HCID 21717659, compound

HRID 1386494Notes

Reaction equation

HRID 1386494 reaction equation
[C:1]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([C:16]2[CH:25]=[CH:24][C:23]3[C:22]([CH3:27])([CH3:26])[CH2:21][CH2:20][C:19]([CH3:29])([CH3:28])[C:18]=3[CH:17]=2)[CH:14]=[CH2:15])=[CH:9][CH:8]=1)([O:3][CH2:4][CH3:5])=[O:2].[OH-].[Na+]>C(O)C>[C:1]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([CH:13]([C:16]2[CH:25]=[CH:24][C:23]3[C:22]([CH3:27])([CH3:26])[CH2:21][CH2:20][C:19]([CH3:28])([CH3:29])[C:18]=3[CH:17]=2)[CH:14]=[CH2:15])=[CH:11][CH:12]=1)([O:3][CH2:4][CH3:5])=[O:2].[CH3:26][C:22]1([CH3:27])[CH2:21][CH2:20][C:19]([CH3:28])([CH3:29])[C:18]2[CH:17]=[C:16]([CH:13]([C:10]3[CH:11]=[CH:12][C:7]([NH2:6])=[CH:8][CH:9]=3)[CH:14]=[CH2:15])[CH:25]=[CH:24][C:23]1=2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 21717627HCID 21717627, compound

Product 2

HCID 21717627HCID 21717627, compoundYield 87.8%HCID 21717659HCID 21717659, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of (Z) N-Carbethoxy-4-[1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2-propenyl]aniline (CB96682) (0.28 g, 1.28 mmol) in 10N sodium hydroxide (3.84 ml, 38.4 mmol) and 1.5 ml of ethanol is brought to 80° C. for 3 hours under an atmosphere of argon and with magnetic stirring. After cooling, the mixture is extracted with dichloromethane (4×25 ml), dried over MgSO4, filtered and evaporated to obtain 0.22 g of a raw orange coloured oil (Z) 4-[1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2-propenyl]aniline (yield=96.5%).

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture is extracted with dichloromethane (4×25 ml)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-3e6373fccfbe4fe595f191f67f8d0c5c
Source dataset
uspto-grants-2001_07
Patent number
US06265423B1

Reaction notes

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