1-Nitroso-2-naphthol → 1,3-Dimethyl-3-Carboethoxy-Spiro-(Indoline-2,3'-(3H)-Naphtho[2,1-b]-(1,4)-Oxazine)

HRID 2181381Notes

Reaction equation

HRID 2181381 reaction equation
[N:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[OH:13])=O.[CH3:14][N:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([CH3:29])([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:16]1=[CH2:30]>C(O)C>[CH3:14][N:15]1[C:16]2([O:13][C:4]3[CH:5]=[CH:6][C:7]4[C:12]([C:3]=3[N:1]=[CH:30]2)=[CH:11][CH:10]=[CH:9][CH:8]=4)[C:17]([CH3:29])([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:18]2[C:23]1=[CH:22][CH:21]=[CH:20][CH:19]=2

Participants

4

Reactant 2

HCID 85801-Nitroso-2-naphtholHCID 224861151,3-Dimethyl-3-carboethoxy-2-methylene-indoline

Product 1

HCID 224861051,3-Dimethyl-3-Carboethoxy-Spiro-(Indoline-2,3'-(3H)-Naphtho[2,1-b]-(1,4)-Oxazine)

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-nitroso-2-naphthol (0.50 g, 2.89 mmol) and 1,3-dimethyl-3-carboethoxy-2-methylene-indoline (0.87 g, 2.77 mmol) in ethanol (70 ml) was heated under nitrogen and refluxed for 2 hrs. The solvent was then evaporated and the residue was chromatographed over silica (ethyl acetate/petroleum ether 1:10). After crystallization in ethanol, the yield of the pure product (colorless crystals) was 0.21 g (16%).

Workup

  1. temperaturerefluxed for 2 hrs
  2. customThe solvent was then evaporated
  3. customthe residue was chromatographed over silica (ethyl acetate/petroleum ether 1:10)
  4. customAfter crystallization in ethanol

Sources & evidence

ORD record
ord-8f80d3a6f69d40c09a96e8a2ce851064
Source dataset
uspto-grants-2005_05
Patent number
US06891038B2

Reaction notes

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