Dimethylformamide → (E)-4-(methoxymethylene)-6-(1H-pyrrol-1-yl)isoquinoline-1,3(2H,4H)-dione

HRID 2236454Notes

Reaction equation

HRID 2236454 reaction equation
[N:1]1([C:6]2[CH:7]=[C:8]3[C:13](=[CH:14][CH:15]=2)[C:12](=[O:16])[NH:11][C:10](=[O:17])[CH2:9]3)[CH:5]=[CH:4][CH:3]=[CH:2]1.CN(C)C=O.[CH:23](OC)(OC)[O:24][CH3:25]>C(OC(=O)C)(=O)C>[CH3:23][O:24]/[CH:25]=[C:9]1/[C:10](=[O:17])[NH:11][C:12](=[O:16])[C:13]2[C:8]/1=[CH:7][C:6]([N:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1)=[CH:15][CH:14]=2

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 9005Trimethyl orthoformateHCID 593003906-(1H-Pyrrol-1-yl)isoquinoline-1,3(2H,4H)-dione

Product 1

HCID 59299993(E)-4-(methoxymethylene)-6-(1H-pyrrol-1-yl)isoquinoline-1,3(2H,4H)-dioneYield 40%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
120 °C

Procedure

6-(1H-pyrrol-1-yl)isoquinoline-1,3(2H,4H)-dione (0.1 g, 0.442 mmol) is dissolved in acetic anhydride (0.6 mL), N,N-dimethylformamide (0.15 mL) and trimethyl orthoformate (0.1 mL, 0.919 mmol). After heating at 120° C. for 0.5 h, it is cooled and the solid is filtered and washed successively with acetic anhydride, ether and hexane to yield 47 mg (40%) solid of the title compound; mp 272-273° C.; HRMS (ESI) m/z calcd for C15H12N2O3 269.09207. found 269.09210 (M+H)+1.

Workup

  1. temperatureit is cooled
  2. filtrationthe solid is filtered
  3. washwashed successively with acetic anhydride, ether and hexane

Sources & evidence

ORD record
ord-37c4e083394c47dcb589e02a2c6639ea
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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