Hydrochloric Acid → 2-Hydrazino-6-(2-methoxy-5-methylphenyl)-4-nitropyridine

HRID 1255202Notes

Reaction equation

HRID 1255202 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1[C:10]1[N:15]=[C:14]([N:16](C(OC(C)(C)C)=O)[NH:17]C(OC(C)(C)C)=O)[CH:13]=[C:12]([N+:32]([O-:34])=[O:33])[CH:11]=1.O1CCOCC1.Cl>O>[NH:16]([C:14]1[CH:13]=[C:12]([N+:32]([O-:34])=[O:33])[CH:11]=[C:10]([C:4]2[CH:5]=[C:6]([CH3:9])[CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[N:15]=1)[NH2:17]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid3×HCID 312751,4-DioxaneHCID 67158740Di-tert-butyl 1-[6-(2-methoxy-5-methylphenyl)-4-nitropyridin-2-yl]hydrazine-1,2-dicarboxylate

Product 1

HCID 671593122-Hydrazino-6-(2-methoxy-5-methylphenyl)-4-nitropyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of the title compound from Example 19 Step B (2.0 g, 2.2 mmol), 23 mL 1,4-dioxane and concentrated HCl (2 mL) was stirred for 14 h. Concentrated HCl (8 mL) was added dropwise. After 1 h, concentrated HCl (4 mL) was added dropwise. After 4 h, the reaction mixture was diluted with water and concentrated to a solid form. The solid was further washed by ether twice to give the crude title compound which was used without further purification: LCMS m/z 275.5 [M+H]+.

Workup

  1. waitAfter 1 h
  2. waitAfter 4 h
  3. concentrationconcentrated to a solid form
  4. washThe solid was further washed by ether twice

Sources & evidence

ORD record
ord-90741c1c7ff8430e98fc217a3ee071ff
Source dataset
uspto-grants-2013_06
Patent number
US08455638B2

Reaction notes

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