4-Amino-1-naphthalenecarboxylic acid hydrochloride → 4-Hydrazino-1-naphthalenecarboxylic Acid Hydrochloride

HRID 259900Notes

Reaction equation

HRID 259900 reaction equation
[ClH:1].[NH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]([OH:15])=[O:14])=[CH:5][CH:4]=1.[N:16]([O-])=O.[Na+]>O.Cl.CC#N>[ClH:1].[NH:2]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]([OH:15])=[O:14])=[CH:5][CH:4]=1)[NH2:16]

Participants

6

Reactant 2

HCID 222621904-Amino-1-naphthalenecarboxylic acid hydrochlorideHCID 23668193Sodium Nitrite

Product 1

HCID 677682744-Hydrazino-1-naphthalenecarboxylic Acid HydrochlorideYield 85.9%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Conditions

Temperature
2.5 °C

Procedure

2.4 g of 4-amino-1-naphthalenecarboxylic acid hydrochloride are mixed at 0° C. with 80 ml of concentrated HCl. A solution of 0.89 g of sodium nitrite in 19 ml of water is added and the mixture is left stirring for 2 hours at 2-3° C. It is cooled to -10° C., and a solution of 9.7 g of stannous chloride dihydrate in 90 ml of concentrated HCl is added slowly. The temperature is allowed to rise to RT and the mixture is kept stirring for 30 minutes. 200 ml of water are added, the mixture is left stirring for 30 minutes and the solid formed is drained. The solid is taken up in MeCN, drained, washed with ether and dried. 2.2 g of the expected product are obtained, m.p.=190° C.

Workup

  1. waitthe mixture is left
  2. temperatureIt is cooled to -10° C.
  3. customto rise to RT
  4. stirringthe mixture is kept stirring for 30 minutes
  5. waitthe mixture is left
  6. stirringstirring for 30 minutes
  7. customthe solid formed
  8. washwashed with ether
  9. customdried

Sources & evidence

ORD record
ord-ace9acd48b4946aba909c44581c473a8
Source dataset
uspto-grants-1996_06
Patent number
US05523455

Reaction notes

Loading…