Triethylamine → Ethyl 2-((5-chloropyridin-2-yl)amino)-2-oxoacetate

HRID 1271707Notes

Reaction equation

HRID 1271707 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.CCN(CC)CC.Cl[C:17](=[O:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19]>C(Cl)Cl.CCOC(C)=O>[CH2:21]([O:20][C:18](=[O:19])[C:17]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1)=[O:23])[CH3:22]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 20884Ethoxalyl chlorideHCID 661742-Amino-5-chloropyridine

Product 1

HCID 1728453Ethyl 2-((5-chloropyridin-2-yl)amino)-2-oxoacetateYield 34%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-amino-5-chloropyridine (0.645 gm 5.0 mmol) in CH2Cl2 (15 mL) was added Et3N (0.80 mL, 6.0 mL, 1.2 eq) followed by addition of ethyl chlorooxoacetate (0.56 mL, 5.0 mmol, 1.0 eq). The mixture was stirred at rt for 2 h. It was diluted with EtOAc; washed with H2O and brine; dried (Na2SO4); and purified by silica gel chromatography to give pure N-(5-chloro-pyridin-2-yl)-oxalamic acid ethyl ester as a white solid (389 mg, yield: 34%). 1H NMR (400 MHz, methanol-d4) δ 8.16 (d, J=2.4 Hz, 1H), 7.97 (d, J=9.4 Hz, 1H), 7.66 (dd, J=8.9, 2.6 Hz, 1H), 4.19 (q, J=6.6 Hz, 2H), 1.20 (t, J=6.6 Hz, 3H) ppm. MS (ESI) 227.0 (M−H).

Workup

  1. washwashed with H2O and brine
  2. dry with materialdried (Na2SO4)
  3. customand purified by silica gel chromatography

Sources & evidence

ORD record
ord-11b9339539064bb082e0d62396f8f1a0
Source dataset
uspto-grants-2007_04
Patent number
US07205318B2

Reaction notes

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