2-Iodoaniline → HCID 12326100, compound

HRID 2215892Notes

Reaction equation

HRID 2215892 reaction equation
[I:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[N:9]([O-])=O.[Na+].[Sn](Cl)[Cl:14]>Cl.O>[ClH:14].[I:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][NH2:9]

Participants

6

Reactant 3

HCID 119952-IodoanilineHCID 24479Stannous ChlorideHCID 23668193Sodium Nitrite

Product 1

HCID 12326100HCID 12326100, compoundYield 96.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

2-Iodoaniline (16 g, 73 mmol) was suspended in concentrated hydrochloric acid (100 mL), and then cooled to 0° C. in an ice bath. Sodium nitrite (6 g, 87.6 mmol) in water (25 mL) was added slowly to reaction mixture and then reaction allowed to stir at 0° C. for 1.5 h. In a separate flask, tin(II) chloride (84.7 g, 182.5 mmol) was dissolved in concentrated hydrochloric acid (12 mL) and added slowly over 30 min to reaction mixture. The resulting suspension was allowed to warm to rt and stirred for 14 h. The solid was filtered off, and allowed to dry to afford 1-(2-iodophenyl)hydrazine hydrochloride (19 g, 96%). 1H NMR (CDCl3, 300 MHz) δ 7.82 (dd, 1H, J=1.1, 7.7 Hz), 7.39 (dt, 1H, 1.2, 7.7 Hz), 6.96 (dd, 1H, J=1.1, 8.1 Hz), 6.82 (dt, 1H, J=1.1, 7.5) ppm. MS (ApCI) 275 (M++CH3CN+H).

Workup

  1. customreaction
  2. additionadded slowly over 30 min to reaction mixture
  3. temperatureto warm to rt
  4. stirringstirred for 14 h
  5. filtrationThe solid was filtered off
  6. customto dry

Sources & evidence

ORD record
ord-b5372da0176d430c97d9de64b73b2f0f
Source dataset
uspto-grants-2006_09
Patent number
US07109339B2

Reaction notes

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