Hydrochloric Acid → 2-Naphthalenecarboxylic acid, 3-(phenylamino)-

HRID 1941065Notes

Reaction equation

HRID 1941065 reaction equation
O[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][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl>>[NH:15]([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)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 71043-Hydroxy-2-naphthoic acid

Product 1

HCID 1388882-Naphthalenecarboxylic acid, 3-(phenylamino)-Yield 7%

Conditions

Temperature
170 °C

Procedure

A mixture of 3-hydroxy-2-naphthoic acid (Aldrich cat. #H4600-7) (376 g, 2.0 mol) and aniline (376 ml, 4.1 mol) was heated at 170° C. with stirring under nitrogen for 16 hours. The resulting mixture, when hot, was poured into 1N HCl (2.5 ml), heated to 100° C., and stirred at this temperature for 5 minutes. The mixture, when hot, was filtrated and the solid was washed with 0.2N HCl (600 ml). The wet material was boiled and mechanically stirred with 0.5N sodium carbonate solution (6.0 ml) for 10 minutes, cooled and filtered. The reddish filtrate was treated dropwise with 5N HCl with stirring to ~ pH 7. The resulting yellow precipitate was collected, washed with small amount of water and crystallized from ethanol (400 ml) to give 3-anilino-2-naphthoic acid (36 g, 7%). Rf 0.6 (silica gel, EM Art. 5715, 20% methanol/chloroform). MS (EI): m/z 264 (M).

Workup

  1. temperatureheated to 100° C.
  2. stirringstirred at this temperature for 5 minutes
  3. filtrationThe mixture, when hot, was filtrated
  4. washthe solid was washed with 0.2N HCl (600 ml)
  5. stirringmechanically stirred with 0.5N sodium carbonate solution (6.0 ml) for 10 minutes
  6. temperaturecooled
  7. filtrationfiltered
  8. additionThe reddish filtrate was treated dropwise with 5N HCl
  9. stirringwith stirring
  10. customThe resulting yellow precipitate was collected
  11. washwashed with small amount of water
  12. customcrystallized from ethanol (400 ml)

Sources & evidence

ORD record
ord-70c066f5926d4011bc266d8422c281bc
Source dataset
uspto-grants-1997_12
Patent number
US05702887

Reaction notes

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