Hydrochloric Acid → HCID 44608378, compound

HRID 1943681Notes

Reaction equation

HRID 1943681 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:13]([N:15]2[CH2:20][CH2:19][O:18][C:17]3[CH:21]=[N:22][CH:23]=[CH:24][C:16]2=3)=[O:14])[CH:5]=[C:6]([N+:10]([O-:12])=[O:11])[C:7]=1[O:8]C.[Cl-].[Li+].N1CCNCC1.C(=O)([O-])O.[Na+].Cl>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:13]([N:15]2[CH2:20][CH2:19][O:18][C:17]3[CH:21]=[N:22][CH:23]=[CH:24][C:16]2=3)=[O:14])[CH:5]=[C:6]([N+:10]([O-:12])=[O:11])[C:7]=1[OH:8]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 4837PiperazineHCID 433294Lithium Chloride2×HCID 516892Sodium BicarbonateHCID 66936726HCID 66936726, compound

Product 1

HCID 44608378HCID 44608378, compoundYield 103.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a 25 ml flask, (3-chloro-4-methoxy-5-nitro-phenyl)-(2,3-dihydro-pyrido[3,4-b][1,4]oxazin-1-yl)-methanone (176 mg, 0.441 mmol), lithium chloride (42.7 mg, 1.006 mmol), piperazine (65 mg, 0.755 mmol) and N,N-dimethyl formamide (5 ml) were added and stirred at 1000 for 30 minutes. Lithium chloride (42.7 mg, 1.006 mmol) was further added thereto and then stirred at 1000 for 2 hours. After neutralizing with saturated solution of sodium hydrogen carbonate to pH 8 to 9, the mixture was adjusted to pH 6 again by using 1N hydrochloric acid to form solid. The resulting solid was filtered and recrystallized from methanol and tetrahydrofuran to obtain the target compound 36 as yellow solid (153 mg, 91%).

Workup

  1. stirringstirred at 1000 for 2 hours
  2. customto form solid
  3. filtrationThe resulting solid was filtered
  4. customrecrystallized from methanol and tetrahydrofuran

Sources & evidence

ORD record
ord-97f2c3372d5243779ce83136a49e6f5e
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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