HCID 59353026, compound → HCID 59353031, compound

HRID 1914688Notes

Reaction equation

HRID 1914688 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[C:16]([N+:18]([O-])=O)[CH:17]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]1)=[O:7]>CC(O)=O.CCO.[Fe]>[CH3:1][O:2][C:3]1[CH:17]=[C:16]([CH:15]=[C:5]([C:6]([N:8]2[CH2:9][CH2:10][N:11]([CH3:14])[CH2:12][CH2:13]2)=[O:7])[CH:4]=1)[NH2:18]

Participants

5

Reactant 1

HCID 59353026HCID 59353026, compound

Product 1

HCID 59353031HCID 59353031, compoundYield 62.3%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

1-(3-Methoxy-5-nitrobenzoyl)-4-methylpiperazine (900 mg; 3.22 mmol; 1 eq) and iron powder (719.82 mg; 12.89 mmol; 4 eq) are heated for 1 h at 100° C. in a mixture of AcOH (10 mL) and EtOH (10 mL). The reaction mixture is cooled down to room temperature, concentrated under vacuum and basified with aqueous Na2CO3. The product is extracted with EtOAc. The organic phase is dried over MgSO4 and the solvent evaporated under reduced pressure to afford 500 mg (62%) of the title compound as an orange oil. 1H NMR (DMSO-d6) δ 6.20-6.17 (m, 1H), 6.11-6.10 (m, 1H), 6.01-5.99 (m, 1H), 5.35-5.27 (m, 2H), 3.66 (s, 3H), 3.55-3.53 (m, 4H), 2.30-2.28 (m, 4H), 2.18 (s, 3H). LC/MS: (ES+): 250.4.

Workup

  1. concentrationconcentrated under vacuum
  2. extractionThe product is extracted with EtOAc
  3. dry with materialThe organic phase is dried over MgSO4
  4. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-b224ac5e0c3e48e6b3c491f92c1560b3
Source dataset
uspto-grants-2013_12
Patent number
US08614215B2

Reaction notes

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