Acetic Anhydride → 1-(1-Methylidene-1,3,4,9-tetrahydro-2H-beta-carbolin-2-yl)ethan-1-one

HRID 1004051Notes

Reaction equation

HRID 1004051 reaction equation
[CH3:1][C:2]1[NH:14][CH2:13][CH2:12][C:4]2=[C:5]3[C:10](=[N:11][C:3]=12)[CH:9]=[CH:8][CH:7]=[CH:6]3.[C:15](OC(=O)C)(=[O:17])[CH3:16].C(OCC)(=O)C>N1C=CC=CC=1>[CH2:1]=[C:2]1[C:3]2[NH:11][C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4]=2[CH2:12][CH2:13][N:14]1[C:15](=[O:17])[CH3:16]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 178421669HCID 178421669, compound

Product 1

HCID 137950311-(1-Methylidene-1,3,4,9-tetrahydro-2H-beta-carbolin-2-yl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of harmalan (1 mmol) in pyridine (2 ml) is added acetic anhydride (1.1 eq). After acid hydrolysis and extraction with ethyl acetate, the crude product is flash-chromatographed (eluent: EtOAc/pet. ether; 50/50). The 1-methylene-2-acetyl-1,2,3,4-tetrahydro-β-carboline elutes off first.

Workup

  1. customthe crude product is flash-chromatographed (eluent: EtOAc/pet. ether; 50/50)

Sources & evidence

ORD record
ord-575cea39bea6408b88fee262c486e284
Source dataset
uspto-grants-2000_04
Patent number
US06048868

Reaction notes

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