HCID 13850358, compound → 5-Formyl-beta-carboline-3-carboxylic acid ethyl ester

HRID 569075Notes

Reaction equation

HRID 569075 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH:18]=1)=[C:15]([CH2:19][OH:20])[CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:2]>ClCCl.[O-2].[O-2].[Mn+4]>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH:18]=1)=[C:15]([CH:19]=[O:20])[CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 13850358HCID 13850358, compound

Product 1

HCID 138503595-Formyl-beta-carboline-3-carboxylic acid ethyl esterYield 50.4%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

5-Hydroxymethyl-beta-carboline-3-carboxylic acid ethyl ester (1.0 g) is stirred in dichloromethane (250 ml) with manganese dioxide (1.5 g) for 16 hours at room temperature (25° C.). After addition of more manganese dioxide (0.75 g) the reaction mixture is stirred for another 16 hours. Then after filtering of the undissolved portion it is evaporated, the residue is recrystallized twice from ethyl acetate. Thus, 0.5 g of 5-formyl-beta-carboline-3-carboxylic acid ethyl ester with a melting point of 273°-276° C. is obtained.

Workup

  1. filtrationThen after filtering of the undissolved portion it
  2. customis evaporated
  3. customthe residue is recrystallized twice from ethyl acetate

Sources & evidence

ORD record
ord-31c47cf9e7fd49379c2df975c8a11748
Source dataset
uspto-grants-1988_03
Patent number
US04731365

Reaction notes

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