Ethanol → HCID 86604897, compound

HRID 646942Notes

Reaction equation

HRID 646942 reaction equation
C[CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]2[C:14]([N+:15]([O-])=O)=[CH:13][CH:12]=[C:11]([N:18]3[CH2:23][CH2:22][N:21]([CH2:24][C:25]([N:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)=[O:26])[CH2:20][CH2:19]3)[N:10]=2)[CH2:5][CH2:4]1.CCO.[NH4+].[Cl-].C([O-])(O)=O.[Na+]>[Fe].O>[NH2:15][C:14]1[C:9]([N:6]2[CH2:5][CH2:4][CH:3]([CH3:2])[CH2:8][CH2:7]2)=[N:10][C:11]([N:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)=[CH:12][CH:13]=1.[N:27]1([C:25](=[O:26])[CH3:24])[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1

Participants

7

Reactant 4

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 68681991HCID 68681991, compound

Product 1

HCID 86604897HCID 86604897, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 2-[4-(4-2-ethyl-3′-nitro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-6′-yl)-piperazin-1-yl]-1-morpholin-4-yl-ethanone (as prepared in the previous step, 0.11 g, 0.25 mmol) in 2:1 EtOH:water (15 mL) was treated with NH4Cl (0.14 g, 2.5 mmol) and was heated to 100° C. Iron powder (70.4 mg, 1.26 mmol) was added and the reaction stirred at 100° C. for 2 h. The reaction was neutralized with saturated aqueous NaHCO3 and extracted with CH2Cl2. The combined organic layers were dried over MgSO4 and concentrated in vacuo to afford the title compound (0.10 g, 98%), which was used immediately in the next reaction.

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a1f155bb5824473dab2a887c4199ab58
Source dataset
uspto-grants-2010_04
Patent number
US07705042B2

Reaction notes

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