Stannous Chloride → HCID 67451538, compound

HRID 571092

Reaction equation

HRID 571092 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 67451538HCID 67451538, compound

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-ac315b3b73a945a7bd623cb7712163ca
Source dataset
uspto-grants-2015_05
Patent number
US09024041B2

Linked notes

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