Methyl chloroformate → HCID 13730776, compound

HRID 1650094Notes

Reaction equation

HRID 1650094 reaction equation
[C:1]([OH:13])(=O)[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.ClC(OC)=O.C(N(CC)CC)C.[CH:26]([C:29]([CH3:38])([N:33]1CC=CC1)[C:30]([NH2:32])=[O:31])([CH3:28])[CH3:27]>O1CCCC1.O>[C:30]([C:29]([NH:33][C:1](=[O:13])[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1)([CH3:38])[CH:26]([CH3:28])[CH3:27])(=[O:31])[NH2:32]

Participants

7

Reactant 4

HCID 6586Methyl chloroformateHCID 7124Quinaldic AcidHCID 8471TriethylamineHCID 23053528HCID 23053528, compound

Product 1

HCID 13730776HCID 13730776, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of quinaldic acid (20 g, 0.116 mol) in tetrahydrofuran (500 ml) cooled to -9° C. is added methyl chloroformate (8.92 ml, 0.116 mol) followed by triethylamine (18.4 ml, 0.139 mol). After 20 minutes α-isopropyl-α-methyl-3-pyrroline-1-acetamide (15.1 g, 0.116 mol) is added and the mixture stirred overnight at room temperature. Water is added and the solution is reduced to 200 ml on a rotorvap. A white solid separates and is filtered off, water washed and dried. Recrystallization from absolute ethanol gives the product mp 179°-180° C., 26.86 g (87%). Anal. calcd. for C16H19N3O2 : C, 67.34; H, 6.73; N, 14.72. Found: C, 67.14; H, 6.17; N, 14.72.

Workup

  1. filtrationA white solid separates and is filtered off
  2. washwater washed
  3. customdried
  4. customRecrystallization from absolute ethanol

Sources & evidence

ORD record
ord-83bb88f8ed314c389a5d08f8ba006a0c
Source dataset
uspto-grants-1990_05
Patent number
US04923504

Reaction notes

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