Guanidine Nitrate → (4R)-4-(4-chloro-3-nitrophenyl)pyrrolidin-2-one

HRID 1799197Notes

Reaction equation

HRID 1799197 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:12][NH:11][C:10](=[O:13])[CH2:9]2)=[CH:4][CH:3]=1.[N+:14]([O-])([OH:16])=[O:15].NC(N)=N>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]2[CH2:12][NH:11][C:10](=[O:13])[CH2:9]2)=[CH:6][C:7]=1[N+:14]([O-:16])=[O:15]

Participants

4

Reactant 2

HCID 10481Guanidine NitrateHCID 1221679(R)-4-(4-Chlorophenyl)pyrrolidin-2-one

Product 1

HCID 66725177(4R)-4-(4-chloro-3-nitrophenyl)pyrrolidin-2-oneYield 95%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

(4R)-4-(4-Chlorophenyl)pyrrolidin-2-one (44 g, 225.6 mmol) was treated with conc. sulfuric acid (220 mL). This solution was cooled in ice. Guanidine nitrate (27.5 g, 225.6 mmol) was added in portions. The reaction mixture was warmed to room temperature and stirred for 1 h. The mixture was then poured into ice. The product crashed out as a pale yellow solid and was filtered, washed with hexane, and dried to give the title compound (51 g, 95% yield). 1H-NMR (400 MHz, CD3OD): δ7.12 d, J=8.4 Hz, 1H), 6.73-6.74 (d, J=4.0 Hz, 1H), 6.52-6.55 (m, 1H), 3.70-3.74 (m, 1H), 3.54-3.62 (m, 1H), 3.32-3.46 (m, 1H), 2.63-2.69 (dd, J=16.4, 8.8 Hz, 1H), 2.37-2.43 (dd, J=16.8, 8.8 Hz, 1H); MS (ESI) m/z 241.05 (M+H)+.

Workup

  1. temperatureThis solution was cooled in ice
  2. additionThe mixture was then poured into ice
  3. filtrationwas filtered
  4. washwashed with hexane
  5. customdried

Sources & evidence

ORD record
ord-30a5db538ec34332b1c1d951a1a4db09
Source dataset
uspto-grants-2013_01
Patent number
US08344028B2

Reaction notes

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