Pyrrolidine → HCID 58098669, compound

HRID 533455Notes

Reaction equation

HRID 533455 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-347c8fe874f14645873c23d4ea8e5cd8
Source dataset
uspto-grants-2014_10
Patent number
US08853230B2

Reaction notes

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