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Diethyl Oxalate → 4,5-Dihydro-5,8-dimethyl-4-oxopyrano[3,2-b]indole-2-carboxylic acid

HRID 46731
Notes
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Reaction equation

HRID 46731 reaction equation
[CH3:1][C:2]([C:4]1[N:5]([CH3:15])[C:6]2[C:11]([C:12]=1[OH:13])=[CH:10][C:9]([CH3:14])=[CH:8][CH:7]=2)=[O:3].[Na].[C:17](OCC)(=O)[C:18]([O:20]CC)=[O:19].[Na][Na]>C(O)C>[CH3:15][N:5]1[C:6]2[CH:7]=[CH:8][C:9]([CH3:14])=[CH:10][C:11]=2[C:12]2[O:13][C:17]([C:18]([OH:20])=[O:19])=[CH:1][C:2](=[O:3])[C:4]1=2
ParticipantsProcedureSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 7268Diethyl OxalateHCID 141233DisodiumHCID 5360545SodiumHCID 125113281,5-dimethyl-3-hydroxy-1H-indol-2-yl methyl ketone

Product 1

HCID 126284314,5-Dihydro-5,8-dimethyl-4-oxopyrano[3,2-b]indole-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent

Procedure

In a manner analogous to that of Example 14, 8.2 g (0.040 mole) of 1,5-dimethyl-3-hydroxy-1H-indol-2-yl methyl ketone (Example 12) was reacted with sodium metal (3.7 g, 0.16 mole) and diethyl oxalate (21.5g, 0.20 mole) in 200 ml absolute ethanol. The red disodium salt intermediate was then converted to the title compound as described in Example 17. Two recrystallization of the final product from DMF-water yielded yellow needles of mpt. 290°.

Sources & evidence

ORD record
ord-9977afb92eca43458dada9068c15f795
Source dataset
uspto-grants-1979_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04175083

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes