1,2-Dichloroethane → HCID 54052846, compound

HRID 1004063Notes

Reaction equation

HRID 1004063 reaction equation
ClC[CH2:3][C:4](Cl)=[O:5].[Cl-].[Al+3].[Cl-].[Cl-].[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:23](=[CH:24][CH:25]=1)[N:22](C(OCC)=O)[C:21]1[CH:20]([CH3:31])[NH:19][CH2:18][CH2:17][C:16]2=1.[OH2:32].Cl[CH2:34][CH2:35]Cl>>[C:4]([N:19]1[CH2:18][CH2:17][C:16]2[C:15]3[CH:14]=[C:13]4[O:12][CH2:11][CH2:34][C:35](=[O:32])[C:25]4=[CH:24][C:23]=3[NH:22][C:21]=2[CH:20]1[CH3:31])(=[O:5])[CH3:3]

Participants

6

Reactant 5

HCID 111,2-Dichloroethane2×HCID 962WaterHCID 693643-Chloropropionyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 18794247HCID 18794247, compound

Product 1

HCID 54052846HCID 54052846, compoundYield 59%

Procedure

3-Chloropropionyl chloride is added to aluminium chloride (4.34 g) in 1,2-dichloroethane (200 mL), followed by ethyl 6-methoxy-1-methyl-2,3,4,9-tetrahydro-1H-β-carboline-9-carboxylate (3 g as a solution in 1,2-dichloroethane). The mixture is stirred overnight at room temperature and then hydrolysed (100 mL of water). Afier separation of the phases by settling and evaporation of the solvent, the crude product is taken up in ethanol (20 mL) and potassium hydroxide solution (20 mL, 6N), and the resulting solution is stirred for 3 h. After evaporation of the ethanol, the crude product is extracted and then recrystallized from ethyl acetate. The 8-acetyl-7-methyl-2,3,4,6,7,8,9, 10-octahydropyrano[2,3-h]-β-carbolin-4-one is thus obtained (59% yield).

Workup

  1. customAfier separation of the phases
  2. customevaporation of the solvent
  3. stirringpotassium hydroxide solution (20 mL, 6N), and the resulting solution is stirred for 3 h
  4. customAfter evaporation of the ethanol
  5. extractionthe crude product is extracted
  6. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-13983e2a296b493c9681ce60bbdb84a5
Source dataset
uspto-grants-2000_04
Patent number
US06048868

Reaction notes

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