HCID 13772048, compound → HCID 13772049, compound

HRID 652596Notes

Reaction equation

HRID 652596 reaction equation
[C:1]1([S:7]([O:10][C:11]2[C:18]([O:19][CH3:20])=[C:17]([N+:21]([O-])=O)[CH:16]=[CH:15][C:12]=2[CH:13]=[O:14])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)(=O)C.O.[Fe]>[C:1]1([S:7]([O:10][C:11]2[C:18]([O:19][CH3:20])=[C:17]([NH2:21])[CH:16]=[CH:15][C:12]=2[CH:13]=[O:14])(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 1

HCID 13772048HCID 13772048, compound

Product 1

HCID 13772049HCID 13772049, compoundYield 66.9%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

The 4-nitrobenzaldehyde from Procedure 3 (82.0 g, 243 mM) in glacial acetic acid (323 ml) and H2O (332 ml) at 90°-95° C. was treated with iron powder (103 g, 40 mesh) added in 10-12 portions during 3/4 hour with vigorous stirring. When addition was complete the suspension was heated at 90°-95° C. for 3 hours. The reaction mixture was cooled and H2O (380 ml) added. The mixture is then filtered and the dark brown solid washed with EtOAc. Removal of solvent afforded 50 g of crude product. Crystallization from EtOAc and treatment with charcoal afford a yellow solid, 50 g (67%), mp 280°-282° C. dec.

Workup

  1. additionadded in 10-12 portions during 3/4 hour with vigorous stirring
  2. additionWhen addition
  3. temperaturewas heated at 90°-95° C. for 3 hours
  4. temperatureThe reaction mixture was cooled
  5. filtrationThe mixture is then filtered
  6. washthe dark brown solid washed with EtOAc
  7. customRemoval of solvent

Sources & evidence

ORD record
ord-7721c4d79cd2420dbcd74602c65d127c
Source dataset
uspto-grants-1987_06
Patent number
US04672116

Reaction notes

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