Sodium Hydroxide → HCID 67278943, compound

HRID 1694390Notes

Reaction equation

HRID 1694390 reaction equation
[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[NH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1.[OH-].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 31268PyrrolidineHCID 357452,3-Dichlorobenzaldehyde

Product 1

HCID 67278943HCID 67278943, compoundYield 80,045%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

NaHB(OAc)3 (15.1 g, 0.0714 mmol) was added under vigorous stirring in portions to a solution of 2,3-dichlorobenzaldehyde (10 g, 0.057 mmol) and pyrrolidine (5.97 mL, 0.0714 mmol) in CH2Cl2 (200 mL). The reaction mixture was vigorously stirred overnight. Then 5N NaOH (50 mL) was added, and the layers were separated. The product was extracted from the aqueous layer with CH2Cl2 (2×50 mL). The combined extracts were washed with 5N NaOH (50 mL), water, brine, dried with anhydrous Na2SO4, and evaporated. The residue was distilled in vacuum to give title compound (10.5 g, 90%) as a colorless liquid (bp 80-84° C./0.5 mmHg). LC/MS data: 229.9, 230.9, 231.9 (M+H) (calculated for C11H13Cl2N 230.14). 1H NMR data (DMSO-d6): δ 7.52 (dd, 1H, J1=1.5 Hz, J2=7.8 Hz), 7.46 (dd, 1H, J1=1.5 Hz, J2=7.8 Hz), 7.33 (t, 1H, J=7.8 Hz), 3.70 (s, 2H), 2.46-2.52 (m, 4H), 1.66-1.75 (m, 4H).

Workup

  1. customthe layers were separated
  2. extractionThe product was extracted from the aqueous layer with CH2Cl2 (2×50 mL)
  3. washThe combined extracts were washed with 5N NaOH (50 mL), water, brine
  4. dry with materialdried with anhydrous Na2SO4
  5. customevaporated
  6. distillationThe residue was distilled in vacuum

Sources & evidence

ORD record
ord-878f8a40cfa149feb3a90a92d9683a51
Source dataset
uspto-grants-2012_04
Patent number
US08158673B2

Reaction notes

Loading…