Methyl chloroformate → N-Ethyl-N-phenyl-4-[(1,2,3,4-tetrahydro-2-oxo-5-quinolinyl)oxy]butanamide

HRID 1154936Notes

Reaction equation

HRID 1154936 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[CH2:10][CH2:11][C:12](=[O:18])[NH:13]2)([OH:3])=O.CN1CCOCC1.ClC(OC)=O.[CH2:31]([NH:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH3:32]>O.C(Cl)Cl>[CH2:31]([N:33]([C:1]([CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[CH2:10][CH2:11][C:12](=[O:18])[NH:13]2)=[O:3])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH3:32]

Participants

7

Reactant 4

HCID 6586Methyl chloroformateHCID 7670N-EthylanilineHCID 79724-MethylmorpholineHCID 12819301HCID 12819301, compound

Product 1

HCID 13200319N-Ethyl-N-phenyl-4-[(1,2,3,4-tetrahydro-2-oxo-5-quinolinyl)oxy]butanamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

2.5 Grams of 5-(3-carboxy)propoxy-3,4-dihydrocarbostyril and 2.0 ml of N-methylmorpholine are added to 200 ml of methylene chloride, and then 1.0 ml of methyl chloroformate is added dropwise to said solution under external ice cooling and agitation while maintaining the internal temperature at 10°-20° C. After this dropwise addition, the mixture is further agitated at room temperature for 30 minutes and then added with 1.3 ml of N-ethylaniline, followed by additional 4-hour agitation at the same temperature. After the reaction, 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 ethanol, consequently obtaining 2.6 g of 5-[3-(N-ethylanilinocarbonyl)propoxy]-3,4-dihydrocarbostyril in the form of colorless needle-like crystals. m.p. 179.5°-180.5° C.

Workup

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

Sources & evidence

ORD record
ord-60349dc66b1046e7bd435f515d7bbf8f
Source dataset
uspto-grants-1981_11
Patent number
US04298739

Reaction notes

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