Diethyl (ethoxymethylene)malonate → HCID 12043739, compound

HRID 2227165Notes

Reaction equation

HRID 2227165 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([I:8])=[C:4]([CH3:9])[N:3]=1.C(O[CH:13]=[C:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16])C>>[I:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][CH:13]=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[N:3][C:4]=1[CH3:9]

Participants

3

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 9596135-Iodo-6-methylpyridin-2-amine

Product 1

HCID 12043739HCID 12043739, compoundYield 83%

Procedure

A solution of 2-amino-5-iodo-6-picoline (Prep 2 4.48 g) and diethyl ethoxymethylenemalonate (4.25 mL) is heated at 95° C. for 1.5 h. The reaction is cooled to room temperature. Hexanes (20 mL) are added and the resulting solid is filtered, washed with a minimal amount of hexanes, and dried to give the desired enamine (6.45 g, 83%). Physical Characteristics are as follows: m.p. 138-139° C.; 1H NMR (300 MHz, DMSO-d6) δ 10.70, 8.96, 8.11, 7.03, 4.21, 4.14, 1.26, 1.24; IR (drift) 2989, 1686, 1641, 1603, 1568, 1548, 1421, 1373, 1363, 1333, 1272, 1251, 1232, 1211, 800 cm−1; MS (ESI) m/z 404.9 (M+H)+, 402.9 (M−H)−; Anal. Calcd for C14H17IN2O4: C, 41.60; H, 4.24; N, 6.93; Found: C, 41.68; H, 4.35; N, 6.83.

Workup

  1. filtrationthe resulting solid is filtered
  2. washwashed with a minimal amount of hexanes
  3. customdried

Sources & evidence

ORD record
ord-7bf2a4ae624845a8bcee80a1607dff6b
Source dataset
uspto-grants-2002_07
Patent number
US06413958B2

Reaction notes

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