Formic Acid → HCID 178518054, compound

HRID 369832Notes

Reaction equation

HRID 369832 reaction equation
[Br-].[NH2:2][C:3]1[NH:7][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N+:9]=2CC2C=CC=CC=2)=[CH:5][C:4]=1[C:21]([O:23]CC)=O.[CH3:26][N:27](C=O)C.C(O)=O>C(N)=O>[N:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:6]1[NH:7][C:3]2[N:2]=[CH:26][N:27]=[C:21]([OH:23])[C:4]=2[CH:5]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 6228DimethylformamideHCID 23282697HCID 23282697, compound

Product 1

HCID 178518054HCID 178518054, compound

Reagents, catalysts & solvents 1

HCID 713FormamideSolvent

Procedure

Under a protective gas, 27.07 g of 2-(5-amino-4-ethoxycarbonyl-1H-pyrrol-2-yl)-N-benzyl-pyridinium bromide in 195 ml of formamide are heated for 16 hours at 150° C. with 97.6 ml of DMF (dried over 4A molecular sieve) and 48.8 ml of formic acid. When the dark-brown reaction mixture is cooled in an ice-bath, the title compound crystallizes and can be filtered off and washed with isopropanol and diethyl ether; 1H-NMR (300 MHz, DMSO-d6): 12.5 and 11.9 (2s, 2H), 8.60 (d, J=7, 1H), 8.05-7.8 (m, 3H), 7.28 (dd, J1 =7, J2 =9, 1H), 7.20 (s, 1H); FAB-MS: (M+H)+ =213.

Workup

  1. temperatureWhen the dark-brown reaction mixture is cooled in an ice-bath
  2. customthe title compound crystallizes
  3. filtrationcan be filtered off
  4. washwashed with isopropanol and diethyl ether

Sources & evidence

ORD record
ord-d6232557f1cb436caeaad1857ee6643c
Source dataset
uspto-grants-2000_10
Patent number
US06140332

Reaction notes

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