1,2-Dichloroethane → Tert-butyl 6-(2-benzoylhydrazino)-5-chloronicotinate

HRID 592297Notes

Reaction equation

HRID 592297 reaction equation
Cl.[Cl:2][C:3]1[C:4]([NH:16][NH2:17])=[N:5][CH:6]=[C:7]([CH:15]=1)[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].[C:18](O)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>CN(C)C=O>[C:18]([NH:17][NH:16][C:4]1[C:3]([Cl:2])=[CH:15][C:7]([C:8]([O:10][C:11]([CH3:13])([CH3:14])[CH3:12])=[O:9])=[CH:6][N:5]=1)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 243Benzoic AcidHCID 8471TriethylamineHCID 181649HOAtHCID 516892Sodium BicarbonateHCID 66690635Tert-butyl 5-chloro-6-hydrazinonicotinate hydrochloride salt

Product 1

HCID 66691260Tert-butyl 6-(2-benzoylhydrazino)-5-chloronicotinate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of tert-butyl 5-chloro-6-hydrazinonicotinate hydrochloride salt (3.0 g, 9.5 mmol) in N,N-dimethylformamide (20 mL) were added benzoic acid (1.62 g, 13.3 mmol), EDC (3.63 g, 19.0 mmol), HOAT (1.29 g, 9.48 mmol) and triethylamine (6.6 mL, 48.4 mmol). The reaction mixture was stirred at 60° C. After 1 h, saturated aqueous sodium bicarbonate was added and the mixture was extracted with ethyl acetate (3×). The combined organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated: LC-MS [M+1]=348.1.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×)
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b50334c62ce842a4a29d15a613477e42
Source dataset
uspto-grants-2016_01
Patent number
US09238647B2

Reaction notes

Loading…