Water → HCID 13851112, compound

HRID 543293Notes

Reaction equation

HRID 543293 reaction equation
Cl.[NH2:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([OH:13])=[CH:10]2)=[CH:5][CH:4]=1.C[O-].[Na+].Cl[CH2:18][C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=1.O>CO.CN(C)C=O>[N:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:27]=[CH:28][C:19]=1[CH2:18][O:13][C:9]1[CH:10]=[C:11]2[C:6]([CH:5]=[CH:4][C:3]([NH2:2])=[CH:12]2)=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 203942-(Chloromethyl)quinolineHCID 10942334Sodium MethoxideHCID 1998689151761-16-1

Product 1

HCID 13851112HCID 13851112, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
10 °C

Procedure

To a suspension of 40.0 g 7-amino-2-naphthol hydrochloride (205 mmol) in 250 mL methanol under nitrogen is added 451 mL of 0.91N sodium methoxide (410 mmol) in methanol. After 1 hour of stirring, the solvent is removed and the residue is taken up in 500 mL dimethylformamide and cooled to 10° C. under nitrogen. A solution of 36.3 g 2-(chloromethyl)quinoline (205 mmol) in 200 mL dimethylformamide is added. After stirring overnight at ambient temperature, the reaction is stripped of solvent, water is added and the precipitate is filtered off, dried and recrystallized from toluene to afford 31.1 g (62%) of white crystals, which is further purified by filtration through Florisil. Recrystallization from toluene affords white crystals, m.p. 164.5°-166.0° C.

Workup

  1. customthe solvent is removed
  2. stirringAfter stirring overnight at ambient temperature
  3. additionis added
  4. filtrationthe precipitate is filtered off
  5. customdried
  6. customrecrystallized from toluene

Sources & evidence

ORD record
ord-a98495dc4d884b31a48206f7bcfcf937
Source dataset
uspto-grants-1987_04
Patent number
US04661596

Reaction notes

Loading…