HCID 22167041, compound → HCID 14054108, compound

HRID 1031940Notes

Reaction equation

HRID 1031940 reaction equation
[CH3:1][C:2]1([CH3:20])[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[C:12]([C:14]1[CH:18]=[CH:17][O:16][C:15]=1[CH3:19])=[O:13]>S(=O)(=O)(O)O>[CH3:1][C:2]1([CH3:20])[C:8]2[C:9](=[C:4]([NH:3][C:12]([C:14]3[CH:18]=[CH:17][O:16][C:15]=3[CH3:19])=[O:13])[CH:5]=[CH:6][CH:7]=2)[CH2:10][CH2:11]1

Participants

3

Reactant 1

HCID 22167041HCID 22167041, compound

Product 1

HCID 14054108HCID 14054108, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

20 ml of 85% sulfuric acid solution was added to 2.5 g (9.3 mmols) of 2,2-dimethyl-N-(2-methyl-3-furan carbonyl)- 1,2,3,4-tetrahydroquinoline under water cooling. The mixture was stirred at room temperature for 1 hour and then left standing overnight. Then, the reaction solution was poured into ice water and extracted from ethyl acetate. The resultant organic layer was sequentially washed with water, aqueous sodium hydrogen carbonate solution, water, and brine and then dried with magnesium sulfate. The dried mixture was concentrated. The concentrated residue was purified by being recrystallized with ethyl acetate/n-hexane, to obtain 2.1 g of white crystals (Compound No. 18 shown in Table 6). The yield was 84%.

Workup

  1. waitleft
  2. waitstanding overnight
  3. extractionextracted from ethyl acetate
  4. washThe resultant organic layer was sequentially washed with water, aqueous sodium hydrogen carbonate solution, water, and brine
  5. dry with materialdried with magnesium sulfate
  6. concentrationThe dried mixture was concentrated
  7. customThe concentrated residue was purified
  8. customby being recrystallized with ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-cef6ead038ec41ceb84c1c7c02d5216e
Source dataset
uspto-grants-1990_09
Patent number
US04956375

Reaction notes

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