Methane → HCID 458797, compound

HRID 1458491Notes

Reaction equation

HRID 1458491 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:6][C:5]=1[CH3:15])([O-])=O.C.[OH:17][S:18]([OH:21])(=[O:20])=[O:19]>CC(O)C.[Pd]>[S:18]([OH:21])([OH:20])(=[O:19])=[O:17].[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:11][CH2:12][CH2:13][CH2:14]2)=[CH:6][C:5]=1[CH3:15]

Participants

6

Reactant 3

HCID 297MethaneHCID 1118Sulfuric AcidHCID 54365860HCID 54365860, compound

Product 1

HCID 458797HCID 458797, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent2×

Procedure

20.25 g (0.098 mole) 1-(4-nitro-3-methylphenyl)pyrrolidine were combined with 2 g Darco KB carbon, 200 ml 2-propanol and 5% Pd/C. The mixture was hydrogenated at 60 psi on a Parr apparatus. When reduction was complete, the mixture was filtered through filter aid and stirred with external cooling in an ice/acetone bath. A cold solution of 10.72 g (0.105 mole) concentrated H2SO4 in 20 ml 2-propanol was added dropwise and stirred for 1 hour. The mixture was filtered, washed 2 times with 2-propanol, and dried in vacuo at 50° C. The final yield was 22.3 g (83%) of off-white solid. MS (solid probe): m/e 176 (free base).

Workup

  1. filtrationthe mixture was filtered
  2. filtrationthrough filter aid
  3. temperaturewith external cooling in an ice/acetone bath
  4. stirringstirred for 1 hour
  5. filtrationThe mixture was filtered
  6. washwashed 2 times with 2-propanol
  7. customdried in vacuo at 50° C

Sources & evidence

ORD record
ord-793f9e08709b43b188dc9bbe4a4f2fe7
Source dataset
uspto-grants-1998_12
Patent number
US05851237

Reaction notes

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