Hydrochloric Acid → HCID 62641980, compound

HRID 1916608Notes

Reaction equation

HRID 1916608 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5](Cl)=[N:6][CH:7]=1.[NH2:12][CH2:13][CH2:14][N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.O.Cl>C(O)CCC>[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([NH:12][CH2:13][CH2:14][N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 13441-PyrrolidineethanamineHCID 70194125-Bromo-2-chloro-3-nitropyridine

Product 1

HCID 62641980HCID 62641980, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
50 °C

Procedure

0.86 mL (5.05 mmol) ethyldiiopropylamine are added to a solution of 600 mg (2.53 mmol) 5-bromo-2-chloro-3-nitropyridine and 0.32 mL (2.53 mmol) 1-(2-aminoethyl)-pyrrolidine in 3 mL n-butanol. The reaction is heated to 50° C. and stirred for one hour at this temperature. The solvent is eliminated i.vac. and the residue is combined with 40 mL water and acidified with 1 M HCl. The aqueous phase is extracted with 20 mL EtOAc and the aqueous phase is then made alkaline with saturated K2CO3 solution. The aqueous phase is extracted with 40 mL EtOAc. The organic phase is dried over Na2SO4 and the solvent is eliminated i.vac.

Workup

  1. extractionThe aqueous phase is extracted with 20 mL EtOAc
  2. extractionThe aqueous phase is extracted with 40 mL EtOAc
  3. dry with materialThe organic phase is dried over Na2SO4

Sources & evidence

ORD record
ord-00cfc6b987ae4538a4b69649d5a793b2
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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