1-Isopropylhydrazine hydrochloride → HCID 89370568, compound

HRID 2280863Notes

Reaction equation

HRID 2280863 reaction equation
[CH2:1]=[C:2]1[CH2:5][CH:4]([C:6](=O)[CH2:7][C:8](=O)[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:3]1.Cl.[CH:17]([NH:20][NH2:21])([CH3:19])[CH3:18]>CCO>[CH:17]([N:20]1[C:6]([CH:4]2[CH2:5][C:2](=[CH2:1])[CH2:3]2)=[CH:7][C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N:21]1)([CH3:19])[CH3:18]

Participants

4

Reactant 2

HCID 855731-Isopropylhydrazine hydrochlorideHCID 89370582HCID 89370582, compound

Product 1

HCID 89370568HCID 89370568, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Compound 8b (6.29 g, 29.9 mmol) was dissolved in dry EtOH (65 mL, denaturated with 5% of MeOH) and isopropyl hydrazine hydrochloride (3.97 g, 35.9 mmol) was added. The reaction mixture was stirred for 3 h at rt. The solvent was removed and to the oily residue were added EA (100 mL), water (50 mL) and sat. NaHCO3 (50 mL) sequentially. The layers were separated and the aq. phase was re-extracted with EA (50 mL). The combined organic phases were washed with brine (70 mL) and dried over anh. Na2SO4. The solvent was removed under vacuum and the residue was dried under reduced pressure. Yield: 7.23 g (contains 3.4% of EtOAc by NMR, recalculated pure yield: 6.98 g, 94%). Crude product 8c is 98% pure by HPLC and NMR. 1H-NMR (CDCl3), δ (ppm): 6.62 (s, 1H), 4.88-4.82 (m, 2H), 4.42-4.32 (m, 3H), 3.56-3.45 (m, 1H), 3.17-3.07 (m, 2H), 2.88-2.79 (m, 2H), 1.49 (d, J=8.0 Hz, 6H), 1.37 (t, J=8.0 Hz, 3H).

Workup

  1. customThe solvent was removed and to the oily residue
  2. additionwere added EA (100 mL), water (50 mL) and sat. NaHCO3 (50 mL) sequentially
  3. customThe layers were separated
  4. extractionthe aq. phase was re-extracted with EA (50 mL)
  5. washThe combined organic phases were washed with brine (70 mL)
  6. dry with materialdried over anh. Na2SO4
  7. customThe solvent was removed under vacuum
  8. customthe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-f9e3464fa29c45a2bd6622cda0141c6e
Source dataset
uspto-grants-2015_09
Patent number
US09139539B2

Reaction notes

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