Diethyl Malonate → HCID 19936582, compound

HRID 258045Notes

Reaction equation

HRID 258045 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[C:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18])[CH2:7][CH2:6][CH2:5]2.[C:20](OCC)(=[O:27])[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23].C1CCN2C(=NCCC2)CC1>C(O)C>[CH3:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:11]1[C:10]2[C:2](=[CH:3][C:4]3[CH2:5][CH2:6][CH2:7][C:8]=3[CH:9]=2)[NH:1][C:20](=[O:27])[C:21]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 19936572HCID 19936572, compound

Product 1

HCID 19936582HCID 19936582, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-amino-6-(2-methylbenzoyl)indan (5.02 g), diethyl malonate (6.4 g) and DBU (0.3 ml) was heated at 170°-180° C. for 1 hour. To this reaction mixture was added ethanol to give crystals of ethyl 4-(2-methylphenyl)-2-oxo-1,2,7,8-tetrahydro-6H-cyclopenta[g]quinoline-3-carboxylate (6.81 g, 98.1%). Recrystallization from ethanol-chloroform gave colorless crystals, m.p. 296°-298° C.

Workup

  1. temperaturewas heated at 170°-180° C. for 1 hour

Sources & evidence

ORD record
ord-a4d4807e73f34052a15ef1b2fc98e33e
Source dataset
uspto-grants-1993_11
Patent number
US05264454

Reaction notes

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