Diethyl Oxalate → HCID 86730066, compound

HRID 2272701Notes

Reaction equation

HRID 2272701 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:14]([NH2:15])=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:4][CH:3]=1.[C:16](OCC)(=O)[C:17]([O:19][CH2:20][CH3:21])=[O:18]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:9]3=[N:10][CH:11]=[CH:12][CH:13]=[C:14]3[N:15]=[C:16]2[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 7268Diethyl OxalateHCID 124454222-N-(4-Chlorophenyl)pyridine-2,3-diamine

Product 1

HCID 86730066HCID 86730066, compound

Conditions

Temperature
140 °C

Procedure

A mixture of N2-(4-chlorophenyl)pyridine-2,3-diamine (C9) (1.8 g, 8.2 mmol) and diethyl ethanedioate (18 g, 123 mmol) was stirred at 140° C. for 18 hours. Purification using silica gel chromatography (Gradient: 16% to 50% ethyl acetate in petroleum ether) provided the product as a brown solid, containing approximately 30% of a contaminant by 1H NMR analysis. Yield: 250 mg, 0.83 mmol, 10%. 1H NMR (400 MHz, CD3OD), product peaks only: δ 8.49 (dd, J=4.8, 1.5 Hz, 1H), 8.31 (dd, J=8.2, 1.4 Hz, 1H), 7.61 (br d, J=8.9 Hz, 2H), 7.52 (dd, J=8.2, 4.6 Hz, 1H), 7.49 (br d, J=8.9 Hz, 2H), 4.34 (q, J=7.2 Hz, 2H), 1.25 (t, J=7.2 Hz, 3H).

Workup

  1. customPurification

Sources & evidence

ORD record
ord-8666af6661524623a1d3e8b758204e08
Source dataset
uspto-grants-2015_09
Patent number
US09120788B2

Reaction notes

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