2-Naphthylamine → 2-Naphthylhydrazine hydrochloride

HRID 709388Notes

Reaction equation

HRID 709388 reaction equation
[N:1]([O-])=O.[Na+].[CH:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][C:6]=1[NH2:15].[Cl:16][Sn]Cl>O.Cl>[ClH:16].[CH:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][C:6]=1[NH:15][NH2:1]

Participants

6

Reactant 3

HCID 70572-NaphthylamineHCID 24479Stannous ChlorideHCID 23668193Sodium Nitrite

Product 1

HCID 5199502-Naphthylhydrazine hydrochlorideYield 63.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

NaNO2 (578 mg, 8.38 mmol) in H2O (1.2 mL) was slowly added (2 min of addition) over a suspension of 2-naphthylamine (800 mg, 5.59 mmol) in HCl ac. 6.0 M (6 mL) cooled in a H2O-ice bath. The resulting solution was stirred in H2O-ice bath for 1 h, and SnCl2 (3.71 g, 19.56 mol) was added slowly (5 min of addition). The resulting suspension was stirred in H2O-ice bath for 3.5 h, and then filtered. The solid was successively washed with H2O at 0° C. (4×8 mL), with H2O at rt (1×8 mL), with Et2O at 0° C. (2×4 mL), with Et2O/hexane (1:1, 2×4 mL) and with hexane (2×5 mL). The solid was dried to yield 690 mg of the desired product (Rf=0.7 (40% AcOEt/hexane), cream solid, 63% yield).

Workup

  1. addition(2 min of addition)
  2. temperature6.0 M (6 mL) cooled in a H2O-ice bath
  3. addition(5 min of addition)
  4. filtrationfiltered
  5. washThe solid was successively washed with H2O at 0° C. (4×8 mL)
  6. customat rt
  7. customat 0° C.
  8. customThe solid was dried

Sources & evidence

ORD record
ord-5263c6e65ea746a18b07d04dec7928e5
Source dataset
uspto-grants-2015_11
Patent number
US09181195B2

Reaction notes

Loading…