Acrylic Acid → HCID 18794236, compound

HRID 1004057Notes

Reaction equation

HRID 1004057 reaction equation
[C:1]([OH:5])(=O)[CH:2]=[CH2:3].[CH2:6]([C:8]1[CH:20]=[C:19]2[C:11]([C:12]3[CH2:13][CH2:14][N:15]=[C:16]([CH3:21])[C:17]=3[NH:18]2)=[CH:10][C:9]=1[O:22][CH3:23])[CH3:7].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>CN(C=O)C>[CH3:23][O:22][C:9]1[CH:10]=[C:11]2[C:12]3[CH2:13][CH2:14][N:15]4[C:16]([C:17]=3[NH:18][C:19]2=[CH:20][C:8]=1[CH2:6][CH3:7])=[CH:21][CH2:3][CH2:2][C:1]4=[O:5]

Participants

5

Reactant 3

HCID 6581Acrylic AcidHCID 199401P,P-Diphenylphosphinic azideHCID 135563260HCID 135563260, compound

Product 1

HCID 18794236HCID 18794236, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Acrylic acid (0.23 mL) is added to a solution of 7-ethyl-6-methoxy-1-methyl-3,4-dihydro-β-carboline (740 mg, 3.05 mmol) in DMF (6 mL), followed by dropwise addition of diphenylphosphoryl azide dissolved in DMF (1.5 mL). The medium is left stirring for 6 h. Separation on silica gel allows the 9-methoxy-10-ethyl-2,3,4,6,7,12-hexahydroindolo[2,3-a]quinolizin4-one to be recovered (23% yield).

Workup

  1. waitThe medium is left
  2. customSeparation on silica gel
  3. customto be recovered (23% yield)

Sources & evidence

ORD record
ord-f29d0bb44d864340ac2dc996213a09b5
Source dataset
uspto-grants-2000_04
Patent number
US06048868

Reaction notes

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