Thiophene → 2-Amino-5-benzoylbenzaldehyde

HRID 1968778Notes

Reaction equation

HRID 1968778 reaction equation
[C:1]([C:9]1[CH:10]=[CH:11][C:12]([N+:17]([O-])=O)=[C:13]([CH:16]=1)[CH:14]=[O:15])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S1C=CC=C1>C1(C)C=CC=CC=1.[Pd]>[NH2:17][C:12]1[CH:11]=[CH:10][C:9]([C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:16][C:13]=1[CH:14]=[O:15]

Participants

5

Reactant 2

HCID 8030ThiopheneHCID 198160555-Benzoyl-2-nitrobenzaldehyde

Product 1

HCID 586251382-Amino-5-benzoylbenzaldehyde

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 5-benzoyl-2-nitrobenzaldehyde (0.01 mol) in toluene was hydrogenated at room temperature and normal pressure with 5% Pd/C (2 g) as a catalyst in the presence of 4% thiophene solution (2 mL). After uptake of H2 gas (3 equiv.), the catalyst was filtered off and the filtrate was evaporated (water bath at 50° C.). The residue was dissolved in diethyl ether (10 mL) and crystallized out at room temperature. The crystals were filtered off, washed with a small amount of diethyl ether and diisopropyl ether, then dried (vacuum, 40° C.) to yield the title compound as a solid.

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationAfter uptake of H2 gas (3 equiv.), the catalyst was filtered off
  3. customthe filtrate was evaporated (water bath at 50° C.)
  4. dissolutionThe residue was dissolved in diethyl ether (10 mL)
  5. customcrystallized out at room temperature
  6. filtrationThe crystals were filtered off
  7. washwashed with a small amount of diethyl ether and diisopropyl ether
  8. customdried (vacuum, 40° C.)

Sources & evidence

ORD record
ord-2af9b8c5a0714799a07953704afbadef
Source dataset
uspto-grants-2013_04
Patent number
US08426429B2

Reaction notes

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