Diethyl (dimethylamino)propanedioate → 5,6-Dihydro-N,N-dimethyl-4H-pyrrolo(3,2,1ij)quinolin-5-amine

HRID 1648321

Reaction equation

HRID 1648321 reaction equation
Br[CH2:2][C:3]1[C:11]2[N:10]=[CH:9]N(C(OC(C)(C)C)=O)[C:7]=2[CH:6]=[CH:5][CH:4]=1.[CH3:19][N:20]([CH:22]([C:28](OCC)=O)[C:23](OCC)=O)[CH3:21]>C1COCC1.CCOCC>[CH3:19][N:20]([CH3:21])[CH:22]1[CH2:28][C:7]2[C:11]3=[C:3]([CH:2]=[CH:9][N:10]3[CH2:23]1)[CH:4]=[CH:5][CH:6]=2

Participants

4

Reactant 2

HCID 2801725Diethyl (dimethylamino)propanedioateHCID 15744964tert-Butyl 4-(bromomethyl)-1H-benzo[d]imidazole-1-carboxylate

Product 1

HCID 114697185,6-Dihydro-N,N-dimethyl-4H-pyrrolo(3,2,1ij)quinolin-5-amine

Reagents, catalysts & solvents 1

HCID 21868444Ether tetrahydrofuranSolvent

Procedure

This compound was prepared by following the procedure of Example 18, but substituting methyl 7-(bromomethyl)-1H-indole-1-carboxylate for t-butyl 4-(bromomethyl) -1 H-benzimidazole-1-carboxylate and diethyl (dimethylamino)malonate for diethyl (dipropylamino) malonate. The bulk of the product was converted to the maleate salt, mp 114°-115° C. from THF/ether.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-919b76de78dd4f969d27b23258461909
Source dataset
uspto-grants-1995_07
Patent number
US05436240

Linked notes

Loading…