N-Methylaniline → HCID 13200328, compound

HRID 1154938Notes

Reaction equation

HRID 1154938 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13](=[O:18])[CH2:12][CH2:11]2)([OH:3])=O.C(N(CC)CC)C.ClC(OCC)=O.[CH3:32][NH:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>O.C(OCC)(=O)C>[CH3:32][N:33]([C:1]([CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13](=[O:18])[CH2:12][CH2:11]2)=[O:3])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

7

Reactant 4

HCID 7515N-MethylanilineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 12819271HCID 12819271, compound

Product 1

HCID 13200328HCID 13200328, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.5 Grams of 6-(3-carboxy)propoxy-3,4-dihydrocarbostyril and 1.6 ml of triethylamine are added to 200 ml of ethyl acetate, and then 1.0 ml of ethyl chloroformate is added dropwise to this solution under external ice cooling and agitation while maintaining the internal temperature at 10°-20° C. After addition, the mixture is further agitated at room temperature for 1 hour and then added with 1.1 ml of N-methylaniline, followed by additional 2-hour agitation. The reaction solution is added with water, and after liquid separation, the organic layer is washed with a dilute aqueous NaOH solution, diluted hydrochloric acid and water in that order and then dried with anhydrous Na2SO4. After filtering out the inorganic matter, the mother liquor is concentrated and the residue is recrystallized from chloroform-petroleum ether to obtain 2.2 g of 6-[3-(N-methylanilinocarbonyl)propoxy]-3,4-dihydrocarbostyril in the form of colorless needlelike crystals, m.p. 129.5°-131.5° C.

Workup

  1. temperatureagitation while maintaining the internal temperature at 10°-20° C
  2. additionAfter addition
  3. waitfollowed by additional 2-hour
  4. customafter liquid separation
  5. washthe organic layer is washed with a dilute aqueous NaOH solution, diluted hydrochloric acid and water in that order
  6. dry with materialdried with anhydrous Na2SO4
  7. filtrationAfter filtering out the inorganic matter
  8. concentrationthe mother liquor is concentrated
  9. customthe residue is recrystallized from chloroform-petroleum ether

Sources & evidence

ORD record
ord-7296e75ae9154bb1b6b6949c54716271
Source dataset
uspto-grants-1981_11
Patent number
US04298739

Reaction notes

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