4-Chlorobenzylamine → HCID 10295685, compound

HRID 1168509Notes

Reaction equation

HRID 1168509 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.C[O-].[Na+].[OH:13][CH2:14][C:15]#[C:16][C:17]1[CH:18]=[C:19]2[C:24]3=[C:25]([CH2:27][C:28]([CH3:30])([CH3:29])[N:23]3[CH:22]=[C:21]([C:31](OCC)=[O:32])[C:20]2=[O:36])[CH:26]=1>CO>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][C:31]([C:21]2[C:20](=[O:36])[C:19]3[C:24]4=[C:25]([CH2:27][C:28]([CH3:30])([CH3:29])[N:23]4[CH:22]=2)[CH:26]=[C:17]([C:16]#[C:15][CH2:14][OH:13])[CH:18]=3)=[O:32])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 660364-ChlorobenzylamineHCID 10942334Sodium MethoxideHCID 12083033HCID 12083033, compound

Product 1

HCID 10295685HCID 10295685, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

4-Chlorobenzylamine (110 μL) and sodium methoxide (25 mg) are added to a solution of ethyl 8-(3-hydroxyprop-1-ynyl)-2,2-dimethyl-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylate (Preparation 14, 153 mg) in methanol (12 mL). The reaction is warmed to 50° C. for 48 hours. The reaction mixture is cooled in a freezer and the resulting white precipitate is filtered and washed with cold methanol, hexane, and ether to give 150 mg of the title compound as white crystals. Physical characteristics: M.p. 228° C. (dec); 1H NMR (DMSO-d6) δ10.43, 8.98, 7.90, 7.66, 7.40, 5.39, 4.54, 4.34, 3.44, 1.66; IR (diffuse reflectance) 2226, 1907, 1646, 1618, 1568, 1538, 1510, 1493, 1434, 1318, 1307, 1223, 1033, 1012, 808 cm−1; MS (EI) m/z 420 (M+); HRMS (FAB) 421.1332 (C24H21ClN2O3+H).

Workup

  1. temperatureThe reaction mixture is cooled in a freezer
  2. filtrationthe resulting white precipitate is filtered
  3. washwashed with cold methanol, hexane, and ether

Sources & evidence

ORD record
ord-d4d00bc748214388abb92be75008c13b
Source dataset
uspto-grants-2003_09
Patent number
US06624159B2

Reaction notes

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