6-Methoxy-2-naphthol → 1,2-Naphthalenedione, 6-methoxy-, 1-oxime

HRID 1389505Notes

Reaction equation

HRID 1389505 reaction equation
[N:1]([O-:3])=O.[Na+].[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([OH:17])[CH:11]=[CH:10]2>O.C(O)(=O)C>[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13]([N:1]=[O:3])=[C:12]([OH:17])[CH:11]=[CH:10]2

Participants

5

Reactant 2

HCID 2886346-Methoxy-2-naphtholHCID 23668193Sodium Nitrite

Product 1

HCID 123836821,2-Naphthalenedione, 6-methoxy-, 1-oxime

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent3×

Procedure

A solution of sodium nitrite (3.19 g) in water (23.6 ml) is slowly added to a stirring solution of 6-methoxy-2-naphthol [8.0 g, prepared as described in Organic Synthesis 49, 90 (1969)] in acetic acid (46 ml) and water (4.6 ml) at 0° C. The resulting slurry is allowed to stand at room temperature for several hours and diluted with water. The solid is collected, washed, dried and crystallized from methanol to give 6-methoxy-1nitroso-2-naphthol, mp 147°-148° C.

Workup

  1. waitto stand at room temperature for several hours
  2. customThe solid is collected
  3. washwashed
  4. customdried
  5. customcrystallized from methanol

Sources & evidence

ORD record
ord-720d9ce0bec8417cb4220b0cdb668339
Source dataset
uspto-grants-1981_01
Patent number
US04244966

Reaction notes

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