Acetic Anhydride → HCID 18794226, compound

HRID 1004046Notes

Reaction equation

HRID 1004046 reaction equation
[C:1](OC(=O)C)(=[O:3])C.[CH3:8][C:9]1[NH:23][CH2:22][CH2:21][C:11]2=[C:12]3[C:17](=[N:18][C:10]=12)[CH:16]=[CH:15][C:14]([O:19][CH3:20])=[CH:13]3>C(O)=O>[CH2:8]=[C:9]1[C:10]2[NH:18][C:17]3[C:12](=[CH:13][C:14]([O:19][CH3:20])=[CH:15][CH:16]=3)[C:11]=2[CH2:21][CH2:22][N:23]1[CH:1]=[O:3]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 178487038HCID 178487038, compound

Product 1

HCID 18794226HCID 18794226, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
50 °C

Procedure

To acetic anhydride (1 ml) cooled to 0° C. is added dropwise formic acid (0.5 ml). The mixture is heated for 15 min. at 50° C. After cooling rapidly to 0° C., 10-methoxyharmalan (200 mg) is added slowly and portionwise and the medium is left stirring for 2 h. The crude product is then taken to dryness and, after separation by chromatography (eluent: EtOAc/pet. ether; 50/50), 1-methylene-2-formyl-6-methoxy-1,2,3,4-tetrahydro-β-carboline is obtained.

Workup

  1. temperatureAfter cooling rapidly to 0° C.
  2. waitportionwise and the medium is left
  3. customafter separation by chromatography (eluent: EtOAc/pet. ether; 50/50)

Sources & evidence

ORD record
ord-6ce7b970c8ed45d7a381057f482fb07e
Source dataset
uspto-grants-2000_04
Patent number
US06048868

Reaction notes

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