(+-)-1-Aminoindan → 4-(2,3-Dihydro-1H-inden-1-ylamino)-6,7-dimethoxy-3-quinoline carboxamide

HRID 1822861Notes

Reaction equation

HRID 1822861 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]([NH2:18])=[O:17].[NH2:19][CH:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][CH2:21]1>CN(C=O)C>[CH:20]1([NH:19][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:16]([NH2:18])=[O:17])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 123445(+-)-1-AminoindanHCID 221702044-Chloro-6,7-dimethoxyquinoline-3-carboxamide

Product 1

HCID 221702134-(2,3-Dihydro-1H-inden-1-ylamino)-6,7-dimethoxy-3-quinoline carboxamideYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-chloro-6,7-dimethoxy-3-quinolinecarboxamide (0.066 g, 0.25 mmol), 1-aminoindan (0.66 mg, 0.50 mmol), 2-butanole (2 ml), DMF (2 ml) was heated for 48 h at 100° C. After cooling, the solution was reduced by evaporation. The residue was dissolved in water (3 ml) and treated with aqueous ammonia. The solid product was fitered off washed with water air dried for 0.5 h, washed again with heptane and dried. The residue was purified by chromatography on silica (CH2Cl2/MeOH) to give 63 mg, (70%) of the title compound as a white solid.

Workup

  1. temperatureAfter cooling
  2. customthe solution was reduced by evaporation
  3. dissolutionThe residue was dissolved in water (3 ml)
  4. additiontreated with aqueous ammonia
  5. washwashed with water air
  6. customdried for 0.5 h
  7. washwashed again with heptane
  8. customdried
  9. customThe residue was purified by chromatography on silica (CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-8a430e7f67c14668958396ca8749f8c8
Source dataset
uspto-grants-2006_05
Patent number
US07037925B2

Reaction notes

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