ethyl 1-(5-chloro-2-nitrobenzyl)-4-methyl-1H-pyrrole-2-carboxylate → HCID 68155862, compound

HRID 1877789Notes

Reaction equation

HRID 1877789 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:20]([O-])=O)=[C:6]([CH:19]=1)[CH2:7][N:8]1[CH:12]=[C:11]([CH3:13])[CH:10]=[C:9]1[C:14]([O:16][CH2:17][CH3:18])=[O:15]>[Br-].[Br-].[Zn+2].C(O)C>[NH2:20][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:19][C:6]=1[CH2:7][N:8]1[CH:12]=[C:11]([CH3:13])[CH:10]=[C:9]1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

4

Reactant 1

HCID 68156028ethyl 1-(5-chloro-2-nitrobenzyl)-4-methyl-1H-pyrrole-2-carboxylate

Product 1

HCID 68155862HCID 68155862, compound

Reagents, catalysts & solvents 2

HCID 10421208Zinc bromideCatalystHCID 702EthanolSolvent

Procedure

Charge 5% platinum(S)/charcoal (2.5 g), and ethyl 1-(5-chloro-2-nitrobenzyl)-4-methyl-1H-pyrrole-2-carboxylate (16.0 g, 49.57 mmoles) to a 500 mL Parr bottle. Add ethanol (200 mL) then zinc dibromide (0.22 equiv; 2.46 g, 10.91 mmoles) and place the mixture under hydrogen at 275.8 kPa and hydrogenate at room temperature overnight, monitoring formation of a partially hydrogenated intermediate. Remove the Parr bottle, heat gently in a water bath to dissolve the crystallized material, and filter through celite. Combine with the filtrate from an identical run and evaporate to give ethyl 1-(2-amino-5-chlorobenzyl)-4-methyl-1H-pyrrole-2-carboxylate an off-white solid. Place under high vacuum to remove residual ethanol to give the material (35 g, quantitative). MS (m/z): 293.1 (M+1).

Workup

  1. customhydrogenate at room temperature
  2. customovernight
  3. customRemove the Parr bottle
  4. temperatureheat gently in a water bath
  5. dissolutionto dissolve the crystallized material
  6. filtrationfilter through celite
  7. customCombine with the filtrate from an identical run and evaporate

Sources & evidence

ORD record
ord-64d6eb8cb12b4ca692eb68c2cccc8c34
Source dataset
uspto-grants-2012_11
Patent number
US08314092B2

Reaction notes

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