Hydrochloric Acid → (2-Fluorobenzyl)hydrazine dihydrochloride

HRID 1973008Notes

Reaction equation

HRID 1973008 reaction equation
[ClH:1].[F:2][C:3]1[CH:21]=[CH:20][CH:19]=[CH:18][C:4]=1[CH2:5][N:6](C(OC(C)(C)C)=O)[N:7]=C(C)C>C1COCC1>[ClH:1].[ClH:1].[F:2][C:3]1[CH:21]=[CH:20][CH:19]=[CH:18][C:4]=1[CH2:5][NH:6][NH2:7]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58529833Tert-butyl 1-(2-fluorobenzyl)-2-isopropylidenehydrazinecarboxylate

Product 1

HCID 56604647(2-Fluorobenzyl)hydrazine dihydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Aqueous hydrochloric acid (3 M, 60.64 mL, 181.92 mmol)I was added to a solution of tert-butyl 1-(2-fluorobenzyl)-2-isopropylidenehydrazinecarboxylate (17 g, 60.64 mmol) in THF (100 mL) and the mixture was heated at reflux for 3 h and concentrated. The residue was taken up in toluene and concentrated, then ether was added to the residue and the suspension was stirred for 30 min and filtered. The filter cake (12.2 g, 94%) was washed with ether and dried on the high vacuum pump. LC-MS [M-2HCl]=141.0, RT=0.25 min.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 3 h
  3. concentrationconcentrated
  4. concentrationconcentrated
  5. additionether was added to the residue
  6. filtrationfiltered
  7. washThe filter cake (12.2 g, 94%) was washed with ether
  8. customdried on the high vacuum pump

Sources & evidence

ORD record
ord-70184066877e404487e34e290e25d121
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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