Methanol → methyl 2-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-2-oxoacetate

HRID 1465917Notes

Reaction equation

HRID 1465917 reaction equation
[CH2:1]1[CH2:10][N:9]2[CH:11]=[CH:12][C:7]3=[C:8]2[C:3](=[CH:4][CH:5]=[CH:6]3)[CH2:2]1.[C:13](Cl)(=[O:17])[C:14](Cl)=[O:15].[CH3:19][OH:20]>>[C:12]1([C:13](=[O:17])[C:14]([O:20][CH3:19])=[O:15])[C:7]2=[C:8]3[C:3](=[CH:4][CH:5]=[CH:6]2)[CH2:2][CH2:1][CH2:10][N:9]3[CH:11]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 65578Oxalyl chlorideHCID 156456291-Azatricyclo[6.3.1.0,4,12]dodeca-2,4,6,8(12)-tetraene

Product 1

HCID 59298805methyl 2-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-2-oxoacetate

Procedure

In one aspect, Step 1 is the reaction of lilolidine with oxalyl chloride in an inert solvent and methanol to form compound C. In one aspect, the amount of oxalyl chloride used with respect to lilolidine is about 1.0 to about 1.2 equivalents. In another aspect, the amount of oxalyl chloride to lilolidine is about 1.05 equivalents.

Sources & evidence

ORD record
ord-9f20389f91e94e61b98bff6fcbd2010a
Source dataset
uspto-grants-2015_04
Patent number
US09000005B2

Reaction notes

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