Stannous Chloride → 2-Methoxy-4-hydrazinylbenzoic acid hydrochloride

HRID 1427409Notes

Reaction equation

HRID 1427409 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:11][CH3:12])[CH:3]=1.[N:13]([O-])=O.[Na+].[Sn](Cl)[Cl:18]>Cl.O>[ClH:18].[CH3:12][O:11][C:4]1[CH:3]=[C:2]([NH:1][NH2:13])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]

Participants

6

Reactant 3

HCID 24479Stannous ChlorideHCID 755994-Amino-o-anisic acidHCID 23668193Sodium Nitrite

Product 1

HCID 674515382-Methoxy-4-hydrazinylbenzoic acid hydrochloride

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 4-amino-2-methoxybenzoic acid (3.00 g, 18.0 mmol) in hydrochoric acid (1.0 M, 30 mL) at 0° C. was added a solution of sodium nitrite (1.28 g, 18.5 mmol) in water (5.0 mL) over 5 min. The reaction mixture was maintained at 0° C. for 5 hr and was then treated with tin(II) chloride (9.53 g, 50.3 mmol) in hydrochloric acid (1M, 60 mL) and warmed to RT for 64 hr. A thick precipitate formed which was isolated by filtration, washed with water (50 mL) and ether (15 mL) and dried in vacuo to afford 2-methoxy-4-hydrazinylbenzoic acid hydrochloride as a beige solid (1.05 g, 90% purity, 24%); Rt 0.17 min (Method 2); m/z 181 (M+H)+, (ES+). This material was used in the subsequent step without further purification.

Workup

  1. temperaturewarmed to RT for 64 hr
  2. customA thick precipitate formed which
  3. customwas isolated by filtration
  4. washwashed with water (50 mL) and ether (15 mL)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-a48fe81523a7413281eebe841e72e46d
Source dataset
uspto-grants-2015_01
Patent number
US08933228B2

Reaction notes

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