Sodium Hydroxide → 1-(2-Methylphenyl)-4-amino-6-methyl-2,3-dihydropyrrolo[3,2-c]quinoline

HRID 729088Notes

Reaction equation

HRID 729088 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([CH3:21])[C:14]=3[NH:13][C:12](=O)[C:11]=2[CH2:10][CH2:9]1.P(N)([NH2:32])(=O)OC1C=CC=CC=1.[OH-].[Na+]>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([CH3:21])[C:14]=3[N:13]=[C:12]([NH2:32])[C:11]=2[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 81954Phenyl phosphorodiamidate2×HCID 9926017HCID 9926017, compound

Product 1

HCID 157498221-(2-Methylphenyl)-4-amino-6-methyl-2,3-dihydropyrrolo[3,2-c]quinolineYield 15.2%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Conditions

Temperature
230 °C

Procedure

Impure 1-(2-methylphenyl)-4-oxo-6-methyl-2,3,4,5-tetrahydropyrrolo[3,2-c]quinoline (10.0 g) and phenyl phosphorodiamidate (12 g) were fused at 230° C. After 30 minutes the mixture was diluted with diphenyl ether (50 ml), further phenyl phosphorodiamidate (4 g) added, and heated for a further 30minutes at 230° C. Aqueous sodium hydroxide was added and the product extracted into dichloromethane. Chromatography (silica gel, 3% methanolic ammonia in dichloromethane) to remove unchanged starting material was followed by recrystallisation from ethanol to yield 1-(2-methylphenyl)-4-amino-6-methyl-2,3-dihydropyrrolo[3,2-c]quinoline (1.51 g), m.p. 173°-174°.

Workup

  1. customwere fused at 230° C
  2. additionadded
  3. extractionthe product extracted into dichloromethane
  4. customChromatography (silica gel, 3% methanolic ammonia in dichloromethane) to remove unchanged
  5. customwas followed by recrystallisation from ethanol

Sources & evidence

ORD record
ord-71b96ad797a44bbf84153fbdb2284278
Source dataset
uspto-grants-1991_09
Patent number
US05051508

Reaction notes

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