Formic Acid → HCID 178518051, compound

HRID 369843Notes

Reaction equation

HRID 369843 reaction equation
[NH2:1][C:2]1[NH:3][C:4]([C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=2)=[CH:5][C:6]=1[C:7](OCC)=[O:8].[CH3:22][N:23](C=O)C.C(O)=O>C(N)=O.C(O)(C)C>[CH:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:20]=[CH:21][C:12]=1[C:4]1[NH:3][C:2]2[N:1]=[CH:22][N:23]=[C:7]([OH:8])[C:6]=2[CH:5]=1

Participants

6

Reactant 3

HCID 284Formic AcidHCID 6228DimethylformamideHCID 232827142-Amino-3-ethoxycarbonyl-5-(naphth-2-yl)-1H-pyrrole

Product 1

HCID 178518051HCID 178518051, compound

Reagents, catalysts & solvents 2

HCID 713FormamideSolventHCID 3776IsopropanolSolvent

Procedure

420 mg (1.5 mmol) of 2-amino-3-ethoxycarbonyl-5-(naphth-2-yl)-1H-pyrrole are stirred in 3 ml of formamide, 1.5 ml of DMF and 0.75 ml of formic acid at 150° C. for 22 hours. The reaction mixture is diluted with approximately 1 ml of isopropanol and filtered. Washing with ethanol, isopropanol and hexane yields the title compound; m.p.>300° C.; 1H-NMR (200 MHz, DMSO-d6): 12.2 (sb), 8.39 (s, 1H), 8.0 (m, 2H), 7.9 (m, 3H), 7.53 (m, 2H), 7.11 (s, 1H).

Workup

  1. filtrationfiltered
  2. washWashing with ethanol, isopropanol and hexane

Sources & evidence

ORD record
ord-6dc9d75172294104a450df2ffd6ae40a
Source dataset
uspto-grants-2000_10
Patent number
US06140332

Reaction notes

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