Sodium Hydroxide → Methyl 8-amino-2-naphthoate

HRID 259901Notes

Reaction equation

HRID 259901 reaction equation
C([NH:4][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[CH:13]=[C:12]([C:15]([O:17][CH3:18])=[O:16])[CH:11]=[CH:10]2)(=O)C.[OH-].[Na+]>CO.Cl>[NH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[CH:13]=[C:12]([C:15]([O:17][CH3:18])=[O:16])[CH:11]=[CH:10]2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 861834518-Acetylamino-2-naphthoic acid, methyl ester

Product 1

HCID 45089581Methyl 8-amino-2-naphthoateYield 86.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A stirred solution of 8.0 g (33 mmoles) of 8-acetylamino-2-naphthoic acid, methyl ester (VI) in 50 mL of methanol and 35 mL of 12N HCl was allowed to reflux for 1.5 hours. The reaction mixture was then cooled to 0° C., and pH adjusted to 6.5 with 10N NaOH. Removal of methanol in vacuo followed by collection of precipitate by vacuum filtration followed by washing with H2O and air drying afforded 5.72 g (yield: 80%) of 8-amino-2-naphthoic acid, methyl ester; 1H-NMR: δ8.62 (s, 1H), 7.99 (dd, J=8.5 Hz, 1.4 Hz, 1H), 7.78 (d, J=8.5 Hz, 1H), 7.36 (m, 1H), 7.25 (d, J=8.4 Hz, 1H), 6.79 (d, J=7.1 Hz, 1H), 4.35 (bs, 2H), 3.95 (s, 3H); MS (DCI) m/e: 218 (MH+).

Workup

  1. temperatureto reflux for 1.5 hours
  2. customRemoval of methanol in vacuo
  3. filtrationfollowed by collection of precipitate by vacuum filtration
  4. washby washing with H2O and air
  5. customdrying

Sources & evidence

ORD record
ord-828006f0353d45d0847132ba59c78cb8
Source dataset
uspto-grants-1996_06
Patent number
US05523457

Reaction notes

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