Stannous chloride dihydrate → (3-Fluoro-4-methoxyphenyl)hydrazine--hydrogen chloride (1/1)

HRID 1508531Notes

Reaction equation

HRID 1508531 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][CH3:10])[NH2:5].[N:11]([O-])=O.[Na+].O.O.[Sn](Cl)[Cl:18]>Cl.O>[ClH:18].[F:1][C:2]1[CH:3]=[C:4]([NH:5][NH2:11])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 5811103-Fluoro-4-methoxyanilineHCID 23668193Sodium Nitrite

Product 1

HCID 44203039(3-Fluoro-4-methoxyphenyl)hydrazine--hydrogen chloride (1/1)

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Procedure

A suspension of 3-fluoro-4-methoxyaniline (1.5871 g, 11.24 mmol) in hydrochloric acid, 37% (14 ml) was diazotized with sodium nitrite (0.776 g, 11.24 mmol) in water (7 mL) and reduced with tin(ii) chloride dihydrate (1.873 mL, 22.49 mmol) in hydrochloric acid, 37% (5 ml) at 0° C. The reaction was then stirred for 20 min at room temperature. The precipitate was collected by filtration. The cake was triturated with ethanol (50 mL, room temp) followed by filtration to give a pale yellow solid as the titled compound. 1H NMR (DMSO-d6, 500 MHz) δ 10.17 (br s, 2H), 8.12 (br s, 1H), 7.10 (dd, J=9.0, 9.0 Hz, 1H), 6.96 (dd, J=13.0, 2.5 Hz, 1H), 6.80-6.76 (m, 1H) 3.76 (s, 3H), 3.42 (br s, 1H).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. customThe cake was triturated with ethanol (50 mL, room temp)
  3. filtrationfollowed by filtration

Sources & evidence

ORD record
ord-eaeb877c5a0f41bd95cb8b7f5b9dcc29
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

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