4-Chlorobenzylamine → N-(4-Chlorobenzyl)-2-(hydroxymethyl)-8-iodo-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxamide

HRID 1168503Notes

Reaction equation

HRID 1168503 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.C([O:13][CH2:14][CH:15]1[N:25]2[C:26]3[C:21]([C:22](=[O:32])[C:23]([C:27](OCC)=[O:28])=[CH:24]2)=[CH:20][C:19]([I:33])=[CH:18][C:17]=3[CH2:16]1)(=O)C>C(Cl)Cl.CCOC(C)=O.CO>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][C:27]([C:23]2[C:22](=[O:32])[C:21]3[C:26]4=[C:17]([CH2:16][CH:15]([CH2:14][OH:13])[N:25]4[CH:24]=2)[CH:18]=[C:19]([I:33])[CH:20]=3)=[O:28])=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 660364-ChlorobenzylamineHCID 12083027Ethyl 2-((Acetyloxy)methyl)-8-iodo-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]-quinoline-5-carboxylate

Product 1

HCID 12083028N-(4-Chlorobenzyl)-2-(hydroxymethyl)-8-iodo-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxamideYield 43%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-chlorobenzylamine (2 mL) and ethyl 2-((acetyloxy)methyl)-8-iodo-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylate (Preparation 9, 0.70 g) is heated to 120° C. under a stream of nitrogen for 7 h, to 100° C. for 18 h, and then to 130° C. for 8 hours. Upon cooling, the mixture is diluted with a mixture of CH2Cl2, EtOAc, and methanol (2/2/1) and absorbed onto silica gel. This material is chromatographed eluting with 0-4% methanol in CH2Cl2 to give a wet brown solid. The crude product is recrystallized by dissolving in hot acetic acid and slowly adding water until cloudiness persisted. Upon standing, crystals form which are collected to provide 340 mg (43%) of the title compound as a tan solid. Physical characteristics: M.p. 222-223° C.; MS (ESI+) m/z 495 (M+H)+.

Workup

  1. temperatureUpon cooling
  2. customabsorbed onto silica gel
  3. customThis material is chromatographed
  4. washeluting with 0-4% methanol in CH2Cl2
  5. customto give a wet brown solid
  6. customThe crude product is recrystallized
  7. dissolutionby dissolving in hot acetic acid
  8. customcrystals form which are collected

Sources & evidence

ORD record
ord-8626b552b82d49aeb0f1c14cc2bc560c
Source dataset
uspto-grants-2003_09
Patent number
US06624159B2

Reaction notes

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