Hydrazine → (2-Chloro-5-iodophenyl)methanamine hydrochloride

HRID 1169876Notes

Reaction equation

HRID 1169876 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([I:20])=[CH:16][C:3]=1[CH2:4][N:5]1C(=O)C2=CC=CC=C2C1=O.NN>CCO>[ClH:1].[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([I:20])=[CH:16][C:3]=1[CH2:4][NH2:5]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 11372903HCID 11372903, compound

Product 1

HCID 11460881(2-Chloro-5-iodophenyl)methanamine hydrochlorideYield 149.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Compound 63 (350 mg, 0.88 mmol) was dissolved in dry EtOH (15 mL) and hydrazine (0.1 mL) was added. The stirred mixture was refluxed for 24 h, cooled and the EtOH evaporated. The residue was dissolved in Et2O (3 mL) and treated with HCl/Et2O. The precipitated hydrochloride salt was filtered and triturated with dry Et2O (3×2 mL), obtaining 200 mg of product (yield 75%). 1H NMR (D2O, 300 MHz) δ 7.88 (s, 1H), 7.80 (dd, J=8.4, 1.8 Hz, 1H), 7.31 (d, J=7.8 Hz, 1H), 4.27 (s, 2H). MS (m/e) (positive FAB) 268.1 (M−Cl)+, m.p. 207-210° C.

Workup

  1. temperatureThe stirred mixture was refluxed for 24 h
  2. temperaturecooled
  3. customthe EtOH evaporated
  4. dissolutionThe residue was dissolved in Et2O (3 mL)
  5. additiontreated with HCl/Et2O
  6. filtrationThe precipitated hydrochloride salt was filtered
  7. customtriturated with dry Et2O (3×2 mL)

Sources & evidence

ORD record
ord-d4b59f654eea411e99ed2a12219d55d7
Source dataset
uspto-grants-2010_11
Patent number
US07825126B2

Reaction notes

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