Acetic Acid → 3-(2-Tert-butoxycarbonyl-2-methylhydrazino)methylene-6-chloro-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline

HRID 653133Notes

Reaction equation

HRID 653133 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12](=[O:15])[CH2:13][CH3:14])[CH2:7][C:6](=[CH:16][N:17](C)C)[C:5]2=[O:20].[C:21]([O:25][C:26]([N:28]([CH3:30])N)=[O:27])([CH3:24])([CH3:23])[CH3:22].C(O)(=O)C>CO.O1CCCC1>[C:21]([O:25][C:26]([N:28]([CH3:30])[NH:17][CH:16]=[C:6]1[C:5](=[O:20])[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=2)[N:8]([C:12](=[O:15])[CH2:13][CH3:14])[CH2:7]1)=[O:27])([CH3:24])([CH3:23])[CH3:22]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 37482801-Boc-1-methylhydrazine2×HCID 54453990HCID 54453990, compound

Product 1

HCID 540949343-(2-Tert-butoxycarbonyl-2-methylhydrazino)methylene-6-chloro-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinolineYield 78%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6-chloro-3-dimethylaminomethylene-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline (2.00 g), 1-tert-butoxycarbonyl-1-methylhydrazine (1.50 g) and acetic acid (1.20 ml) in methanol (100 ml) and tetrahydrofuran (100 ml) was refluxed for 9 hours with stirring. 1-tert-Butoxycarbonyl-1-methylhydrazine (1.50 g) was added to the mixture and the stirring was continued for 8 hours at reflux conditions. After the solvent was evaporated in vacuo, saturated aqueous sodium hydrogen carbonate (15 ml) was added to the mixture and extracted with ethyl acetate (30 ml). The extract was washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue (3.90 g) was chromatographed on silica gel by eluting with chloroform to give 3-(2-tert-butoxycarbonyl-2-methylhydrazino)methylene-6-chloro-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline (2.10 g) as yellow amorphous.

Workup

  1. temperatureat reflux conditions
  2. customAfter the solvent was evaporated in vacuo, saturated aqueous sodium hydrogen carbonate (15 ml)
  3. additionwas added to the mixture
  4. extractionextracted with ethyl acetate (30 ml)
  5. washThe extract was washed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue (3.90 g) was chromatographed on silica gel
  9. washby eluting with chloroform

Sources & evidence

ORD record
ord-3d9e037032af4741b155466954806f96
Source dataset
uspto-grants-1987_06
Patent number
US04675324

Reaction notes

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