3-Amino-2-naphthoic acid → 3-Hydrazino-2-naphthoic acid

HRID 968364Notes

Reaction equation

HRID 968364 reaction equation
[NH2:1][C:2]1[C:3]([C:12]([OH:14])=[O:13])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[N:15]([O-])=O.[Na+].Cl[Sn]Cl.O>Cl.O>[NH:1]([C:2]1[C:3]([C:12]([OH:14])=[O:13])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2)[NH2:15]

Participants

6

Reactant 3

HCID 222443-Amino-2-naphthoic acidHCID 23668193Sodium NitriteHCID 43835034Tin dichloride dihydrate

Product 1

HCID 47388533-Hydrazino-2-naphthoic acid

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

To 3-amino-2-naphthoic acid (15 g, 66.8 mmol) in conc. HCl (100 ml) and water (100 ml) at 0° C. was added NaNO2 (9.22 g, 69 mmol) in 1 g portions while maintaing the reaction temperature below 0° C. After 30 min below 0° C., SnCl2·H2O (75 g) was added in portions over 20 min. The ice bath was removed and stirred at ambient temperature for 1 h. Reaction was filtered and the filter cake washed with water and air dried. The crude material containing tin (II) salts was used as is and gave a mp>300° C.

Workup

  1. customthe reaction temperature below 0° C
  2. customThe ice bath was removed
  3. customReaction
  4. filtrationwas filtered
  5. washthe filter cake washed with water and air
  6. customdried
  7. additionThe crude material containing tin (II) salts
  8. customgave a mp>300° C.

Sources & evidence

ORD record
ord-2cc32428797d4d0192b10c301cc0c607
Source dataset
uspto-grants-2005_10
Patent number
US06958356B2

Reaction notes

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