Water → Methyl 4-[N-methyl-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl) acryloylamino]benzoate

HRID 2268208Notes

Reaction equation

HRID 2268208 reaction equation
[H-].[Na+].[CH3:3][C:4]1([CH3:31])[CH2:13][CH2:12][C:11]([CH3:15])([CH3:14])[C:10]2[CH:9]=[C:8]([CH:16]=[CH:17][C:18]([NH:20][C:21]3[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=3)=[O:19])[CH:7]=[CH:6][C:5]1=2.I[CH3:33].O>CN(C=O)C>[CH3:33][N:20]([C:18](=[O:19])[CH:17]=[CH:16][C:8]1[CH:7]=[CH:6][C:5]2[C:4]([CH3:31])([CH3:3])[CH2:13][CH2:12][C:11]([CH3:14])([CH3:15])[C:10]=2[CH:9]=1)[C:21]1[CH:22]=[CH:23][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 70214611Methyl 4-[3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)acryloylamino]benzoate

Product 1

HCID 70217190Methyl 4-[N-methyl-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl) acryloylamino]benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

300 mg (10 mmol) of sodium hydride (80% in oil) and 30 ml of DMF are introduced into a three-necked flask under a stream of nitrogen. A solution of 1.8 g (4.8 mmol) of methyl 4-[3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl) acryloylamino]benzoate (prepared in Example 2 (a)) in 50 ml of DMF is added dropwise and the mixture is stirred until the evolution of gas has ceased. 750 μl (12 mmol) of iodomethane are then added and the mixture is stirred at room temperature for four hours. The reaction medium is poured into water and extracted with ethyl ether, and the organic phase is separated out after settling has taken place, dried over magnesium sulphate and evaporated. The solid obtained is triturated from hexane, filtered off and dried. 1.6 g (83%) of the expected methyl ester, with a melting point of 167-8° C., are collected.

Workup

  1. stirringthe mixture is stirred at room temperature for four hours
  2. extractionextracted with ethyl ether
  3. customthe organic phase is separated out after settling
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customThe solid obtained
  7. customis triturated from hexane
  8. filtrationfiltered off
  9. customdried
  10. custom1.6 g (83%) of the expected methyl ester, with a melting point of 167-8° C., are collected

Sources & evidence

ORD record
ord-a6994e9953d143cd8e4658b49ba29913
Source dataset
uspto-grants-2001_12
Patent number
US06326510B1

Reaction notes

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