Ethanol → HCID 178469688, compound

HRID 2227166Notes

Reaction equation

HRID 2227166 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]([NH:9][CH:10]=[C:11]([C:17]([O:19]CC)=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N:6][C:7]=1[CH3:8].C(O)C>C1(OC2C=CC=CC=2)C=CC=CC=1>[OH:19][C:17]1[C:4]2[C:5](=[N:6][C:7]([CH3:8])=[C:2]([I:1])[CH:3]=2)[N:9]=[CH:10][C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

4

Reactant 2

HCID 702EthanolHCID 12043739HCID 12043739, compound

Product 1

HCID 178469688HCID 178469688, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

A solution of diethyl 2-{[(5-iodo-6-methyl-2-pyridinyl)amino]methylene}malonate Prep 3(1.09 g) in 20 mL diphenyl ether is heated at 250° C. for 2 h with removal of ethanol via a Dean-Stark trap. The reaction is cooled to room temperature. Hexanes (15 mL) are added and the solid is filtered, washed thoroughly with hexanes, and dried. The crude solid is dissolved in CH2Cl2/MeOH and adsorbed onto silica. Purification by chromatography (eluent CH2Cl2 (1L), 1% MeOH/CH2Cl2 (1L), 2% MeOH/CH2Cl2 (2L)) affords the product as a yellow-green solid (0.50 g, 52%). Physical characteristics are as follows: m.p. 275-277° C. (dec.); 1H NMR (300 MHz, DMSO-d6) δ 12.80, 8.72, 8.47, 4.21, 2.74, 1.27; IR (drift) 2981, 1718, 1606, 1524, 1407, 1376, 1356, 1319, 1291, 1244, 1192, 1185, 1109, 809, 623 cm−1; MS (ESI) m/z 358.9 (M+H)+, 356.9 (M−H)−; Anal. Calcd for C12H11IN2O3: C, 40.24; H, 3.10; N, 7.82; Found: C, 40.15; H, 3.05; N, 7.81.

Workup

  1. filtrationthe solid is filtered
  2. washwashed thoroughly with hexanes
  3. customdried
  4. dissolutionThe crude solid is dissolved in CH2Cl2/MeOH
  5. customPurification by chromatography (eluent CH2Cl2 (1L), 1% MeOH/CH2Cl2 (1L), 2% MeOH/CH2Cl2 (2L))

Sources & evidence

ORD record
ord-6d865d2dfd7c4937befbeef6ceadd20c
Source dataset
uspto-grants-2002_07
Patent number
US06413958B2

Reaction notes

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