Tert-Butylamine → HCID 86629450, compound

HRID 599293Notes

Reaction equation

HRID 599293 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([Cl:13])[CH:3]=1.[C:14]([NH2:18])([CH3:17])([CH3:16])[CH3:15]>>[C:14]([NH:18][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([Cl:13])[CH:3]=1)([CH3:17])([CH3:16])[CH3:15]

Participants

3

Reactant 2

HCID 6385Tert-ButylamineHCID 600045Ethyl 4,6-dichloropyridine-3-carboxylate

Product 1

HCID 86629450HCID 86629450, compoundYield 60%

Procedure

A solution of ethyl 4,6-dichloronicotinate (10 g, 45.7 mmol) in tert-butylamine (100 mL) was stirred at 50° C. for 10 h. The solvent was removed under reduced pressure and the residue was suspended in H2O and extracted with EtOAc (3×100 mL). The organics were washed with brine, dried (MgSO4), concentrated in vacuo and purified by silica gel chromatography to provide ethyl 4-(tert-butylamino)-6-chloronicotinate (7 g, 60% yield). 1HNMR (400 MHz, DMSO-d6): δ 8.53 (s, 1 H), 8.39 (s, 1 H), 6.80 (s, 1 H), 4.25 (d, J=7.2 Hz, 2H), 1.37 (s, 9 H), 1.27 (t, J=7.2 Hz, 3 H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionextracted with EtOAc (3×100 mL)
  3. washThe organics were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-881a090f15f6467793d35028ef98d44a
Source dataset
uspto-grants-2011_03
Patent number
US07897762B2

Reaction notes

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