Pyrrolidine → HCID 58098669, compound

HRID 384254Notes

Reaction equation

HRID 384254 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-])=O)[CH:5]=1)=[C:2]=[O:3].[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1>C(Cl)Cl>[NH2:10][C:6]1[CH:5]=[C:4]([NH:1][C:2]([N:13]2[CH2:17][CH:16]=[CH:15][CH2:14]2)=[O:3])[CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 768353-Nitrophenyl isocyanate

Product 1

HCID 58098669HCID 58098669, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-isocyanato-3-nitrobenzene (1.125 g, 6.18 mmoles) and pyrrolidine (485 mg, 6.8 mmoles) in DCM (20 mL) was stirred at r.t. for 14 hrs. After concentrated, the mixture was extracted with ethyl acetate. The organic layer was washed with aqueous citric acid solution and dried over MgSO4, followed by hydrogenation with Pd/C (wet, 10%, 0.15 g) under a hydrogen balloon overnight. After filtration and concentration, the reasonable pure N-(3-aminophenyl)-2,5-dihydro-1H-pyrrole-1-carboxamide (3, 1.44 g) was used for the next reactions. MS+: 224.2, UV: λ=271.6 nm. 1H NMR: (DMSO) δ7.44 (s, 1H), δ6.78 (m, 1H), δ6.20 (m, 1H), δ3.32 (m, 4H), δ1.83 (m, 4H).

Workup

  1. concentrationAfter concentrated
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with aqueous citric acid solution
  4. dry with materialdried over MgSO4
  5. customballoon overnight
  6. filtrationAfter filtration and concentration

Sources & evidence

ORD record
ord-c76cf9f215c342b8aa8ce4f7ab6da9b8
Source dataset
uspto-grants-2013_02
Patent number
US08367689B2

Reaction notes

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