Hydrochloric Acid → HCID 178493285, compound

HRID 2239511Notes

Reaction equation

HRID 2239511 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]=1[C:12](=[O:14])[CH3:13].Cl.[N:16]([O-])=O.[Na+].[NH:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1>O.[OH-].[K+]>[CH3:9][O:8][C:6]1[C:5]([O:10][CH3:11])=[CH:4][C:3]([C:12](=[O:14])[CH3:13])=[C:2](/[N:1]=[N:16]/[N:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)[CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 31268PyrrolidineHCID 602085Ethanone, 1-(2-amino-4,5-dimethoxyphenyl)-HCID 23668193Sodium Nitrite

Product 1

HCID 178493285HCID 178493285, compoundYield 85.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 14797Potassium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

To a 100 mL round bottom flask charged with a magnetic stir bar and 1-(2-amino-4,5-dimethoxyphenyl)ethanone (1.23 g, 6.29 mmol) was added water (4 mL). The mixture was cooled to 0° C. with an ice bath and concentrated aqueous HCl (1.95 mL) was added to the reaction mixture. With efficient stirring, a solution of sodium nitrite (0.434 g, 6.9 mmol) in water (3 mL) was added to the reaction mixture via Pasteur pipette. The reaction was allowed to stir for 5 minutes at this temperature followed by the slow addition of a solution of pyrrolidine (0.447 g, 6.30 mmol) in 50 mL of 0.4 N aqueous potassium hydroxide. The reaction was allowed to stir at this temperature for 0.5 h before being poured into a separatory funnel and extracted with DCM (2×100 mL). The combined organic extract was dried with MgSO4, filtered, and concentrated in vacuo to yield the crude product which was purified on 80 g of silica using hexanes/EtOAc (1:1) as eluent to give 1.49 g (85%) of the title compound as a brown solid. 1H NMR: 7.12 (s, 1H), 7.01 (s, 1H), 3.92 (m, 2H), 3.80 (s, 3H), 3.75 (s, 3H), 3.58 (m, 2H), 2.60 (s, 3H), 2.00 (M, 4H); m/z: 278.

Workup

  1. additionTo a 100 mL round bottom flask charged with a magnetic stir bar
  2. stirringto stir at this temperature for 0.5 h
  3. additionbefore being poured into a separatory funnel
  4. extractionextracted with DCM (2×100 mL)
  5. extractionThe combined organic extract
  6. dry with materialwas dried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto yield the crude product which
  10. customwas purified on 80 g of silica

Sources & evidence

ORD record
ord-d77550f80b2c463f9e0244fac7610ef9
Source dataset
uspto-grants-2010_05
Patent number
US07723337B2

Reaction notes

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