Water → HCID 66725171, compound

HRID 1799188Notes

Reaction equation

HRID 1799188 reaction equation
N[C:2]1[CH:3]=[C:4]([C@@H:12]2[CH2:16][NH:15][C:14](=[O:17])[CH2:13]2)[C:5]([N+:9]([O-:11])=[O:10])=[CH:6][C:7]=1[Cl:8].N([O-])=O.[Na+].O>OS(O)(=O)=O>[Cl:8][C:7]1[CH:2]=[CH:3][C:4]([C@@H:12]2[CH2:16][NH:15][C:14](=[O:17])[CH2:13]2)=[C:5]([N+:9]([O-:11])=[O:10])[CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 23668193Sodium NitriteHCID 66724941HCID 66724941, compound

Product 1

HCID 66725171HCID 66725171, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of (4R)-4-(3-amino-4-chloro-6-nitrophenyl)pyrrolidin-2-one (3.5 g, 13.7 mmol) in 12.6 mL of conc. H2SO4 was heated to 55° C. Sodium nitrite (16.94 mmol) was added in small portions. The reaction mixture turned from yellow to red, then dark red. After the mixture was stirred for additional 30 min at this temperature, the mixture was cooled to room temperature and water was added. The mixture was then extracted with ethyl acetate (3×30 mL). The combined organic phases were washed with water and brine, and dried over Na2SO4. The solvent was removed in vacuo to afford the title compound (2.5 g, 80% yield). 1H-NMR (400 MHz, CD3OD): δ 2.45-2.51 (dd, J=17.2, 6.8 Hz, 1H), 2.77-2.84 (dd, J=17.2, 9.2 Hz, 1H), 3.41-3.44 (m, 1H), 3.80-3.85 (dd, J=10.4, 8.0 Hz, 1H), 4.03-4.05 (m, 1H), 7.61-7.63 (d, J=8.4 Hz, 1H), 7.67-7.70 (dd, J=8.4, 2.0 Hz, 1H), 7.91 (d, J=2.0 Hz, 1H); MS (ESI) m/z 241.01 (M+H)+.

Workup

  1. extractionThe mixture was then extracted with ethyl acetate (3×30 mL)
  2. washThe combined organic phases were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-a69e92261aa049ce97fbd621950a6756
Source dataset
uspto-grants-2013_01
Patent number
US08344028B2

Reaction notes

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