Water → HCID 66665338, compound

HRID 1773549Notes

Reaction equation

HRID 1773549 reaction equation
[OH-:1].[Na+].[C:3]([C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[C:10]([O:19][CH3:20])[C:11]([NH:15]C(=O)C)=[CH:12]2)=[CH:7][CH:6]=1)#N.[OH2:21]>C(O)CO>[NH2:15][C:11]1[CH:12]=[C:13]2[C:8]([CH:7]=[CH:6][C:5]([C:3]([OH:21])=[O:1])=[CH:14]2)=[CH:9][C:10]=1[O:19][CH3:20]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 66664935HCID 66664935, compound

Product 1

HCID 66665338HCID 66665338, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
195 °C

Procedure

Sodium hydroxide (0.17 g, 4.17 mmol) was added to a suspension of N-(7-cyano-3-methoxy-naphthalen-2-yl)-acetamide (0.2 g, 0.83 mmol) in ethylene glycol (2 mL) and the resulting mixture was heated at reflux (195° C.) overnight. The reaction mixture was then cooled, water was added and the pH was adjusted to 4. The precipitate was collected by filtration and dried to give 0.156 g of 7-amino-6-methoxy-naphthalene-2-carboxylic acid as a brown solid. MS=218 [M+H]+.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureThe reaction mixture was then cooled
  3. filtrationThe precipitate was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-ffe991b0e11940a690e91cff9a763373
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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