methyl 5-tert-butyl-3-nitro-1H-pyrrole-2-carboxylate → methyl 3-amino-5-(tert-butyl)-1H-pyrrole-2-carboxylate

HRID 635243

Reaction equation

HRID 635243 reaction equation
[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:8][C:9]=1[N+:10]([O-])=O)=[O:4]>CO.[Pd]>[NH2:10][C:9]1[CH:8]=[C:7]([C:13]([CH3:16])([CH3:14])[CH3:15])[NH:6][C:5]=1[C:3]([O:2][CH3:1])=[O:4]

Participants

4

Reactant 1

HCID 18322358methyl 5-tert-butyl-3-nitro-1H-pyrrole-2-carboxylate

Product 1

HCID 18322367methyl 3-amino-5-(tert-butyl)-1H-pyrrole-2-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A Parr hydrogenation bottle fitted with a 16×100 mm disposable glass culture tube is charged with methyl-5-t-butyl-3-nitropyrrole-2-carboxylate (14 mg, 0.062 mmol) in dry methanol (1 mL) and Pd (10% on carbon, 3 mg). The reaction is successively evacuated and purged with H2 gas three times. The reaction mixture is then shaken under an atmosphere of H2 (35 psi) for 1 h, diluted with dichloromethane and filtered through celite. The filtrate is concentrated in vacuo to give methyl 3-amino-5-t-butylpyrrole-2-carboxylate as a bright yellow oil (100%, crude yield). 1H NMR (CDCl3) d 7.89 (br s, 2H), 5.52 (d, 1H, J=2.8 Hz), 3.82 (s, 3H), 1.26 (s, 9H).

Workup

  1. customA Parr hydrogenation bottle fitted with a 16×100 mm disposable glass culture tube
  2. customThe reaction is successively evacuated
  3. custompurged with H2 gas three times
  4. additiondiluted with dichloromethane
  5. filtrationfiltered through celite
  6. concentrationThe filtrate is concentrated in vacuo
  7. customto give

Sources & evidence

ORD record
ord-1df8f1d6d7564b018cbf5555f6925960
Source dataset
uspto-grants-2001_02
Patent number
US06187799B1

Linked notes

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