Sulfuric Acid → HCID 69853761, compound

HRID 1458490Notes

Reaction equation

HRID 1458490 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[CH3:11].[NH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1.C([O-])([O-])=O.[Na+].[Na+].C(OCCO)C.[OH:29][S:30]([OH:33])(=[O:32])=[O:31]>CC(O)C>[S:30]([OH:33])([OH:32])(=[O:31])=[O:29].[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[C:3]([CH3:11])[CH:4]=1

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 8076Glycol monoethyl etherHCID 10340Sodium CarbonateHCID 31268PyrrolidineHCID 68001Benzene, 1-fluoro-2-methyl-4-nitro-

Product 1

HCID 69853761HCID 69853761, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

15.5g (0.1 mole) 2-fluoro-5-nitrotoluene, 25 ml (0.3 mole) pyrrolidine, 11.0 g Na2CO3 were combined with 50 ml 2-ethoxyethanol and refluxed with stirring. When the TLC showed no evidence of starting material (ca. 2 hours), the mixture was poured onto ice. The precipitate was filtered, washed 5 times with cold H2O, and dried on filter paper for 2 hours. The resulting solid was mixed with 125 ml 2-propanol, 10% Pd/C, and hydrogenated at 60 psi on a Parr apparatus. The mixture was filtered through filter-aid and stirred with external cooling in an ice/acetone bath. A cold solution of 10.7 g (0.105 mole) concentrated H2SO4 in 15 ml 2-propanol was added dropwise over 15 minutes. The resultant precipitate was filtered, washed 2 times with 2-propanol and dried in vacuo at 50° C. The final yield was 24.45 g (89%) of a light grey solid. MS (solid probe): m/e 176 (free base).

Workup

  1. temperaturerefluxed
  2. customno evidence of starting material (ca. 2 hours)
  3. additionthe mixture was poured onto ice
  4. filtrationThe precipitate was filtered
  5. washwashed 5 times with cold H2O
  6. customdried
  7. filtrationon filter paper for 2 hours
  8. additionThe resulting solid was mixed with 125 ml 2-propanol, 10% Pd/C
  9. filtrationThe mixture was filtered
  10. filtrationthrough filter-aid
  11. stirringstirred
  12. temperaturewith external cooling in an ice/acetone bath
  13. filtrationThe resultant precipitate was filtered
  14. washwashed 2 times with 2-propanol
  15. customdried in vacuo at 50° C

Sources & evidence

ORD record
ord-6f30e0f6f26f4310b637351b40220d2d
Source dataset
uspto-grants-1998_12
Patent number
US05851237

Reaction notes

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