Dimethylformamide → HCID 23369658, compound

HRID 1900724Notes

Reaction equation

HRID 1900724 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]1[O:24][C:13]2=[C:14]3[C:19](=[C:20](I)[CH:21]=[C:12]2[CH2:11]1)[NH:18][C:17](=[O:23])[CH:16]=[CH:15]3)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:25][N:26](C)C=O>>[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]1[O:24][C:13]2=[C:14]3[C:19](=[C:20]([C:25]#[N:26])[CH:21]=[C:12]2[CH2:11]1)[NH:18][C:17](=[O:23])[CH:16]=[CH:15]3)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 23369570HCID 23369570, compound

Product 1

HCID 23369658HCID 23369658, compound

Conditions

Temperature
150 °C

Procedure

2-(t-Butoxycarbonyl)aminomethyl-5-iodo-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one (610 mg) and cuprous cyanide (134 mg) were dissolved in dimethylformamide (30.5 ml), and stirred at 150° C. for 1 hour. After completion of the reaction, the solvent was distilled off, and the residue was purified by silica gel column chromatography (eluent=chloroform:methanol=70:1). As a result, 347 mg of 2-(t-butoxycarbonyl)aminomethyl-5-cyano-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one was obtained (73.7%). This compound was recrystallized from a solvent mixture of chloroform-n-hexane to obtain pale yellow powdery crystals (mp.: 200°-202° C. (dec.)).

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. customthe residue was purified by silica gel column chromatography (eluent=chloroform:methanol=70:1)

Sources & evidence

ORD record
ord-09614b7625f14ccca08c4d4f3e13e8f5
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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