(3-Amino-2-methylphenyl)methanol → HCID 11726290, compound

HRID 1090634Notes

Reaction equation

HRID 1090634 reaction equation
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1Cl)=[CH:13][CH:12]=[CH:11][C:10]=2[O:17][CH3:18])(=[O:5])[CH2:2][CH2:3][CH3:4].[NH2:19][C:20]1[C:21]([CH3:28])=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23][OH:24]>O1CCOCC1>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:19][C:20]1[CH:27]=[CH:26][CH:25]=[C:22]([CH2:23][OH:24])[C:21]=1[CH3:28])=[CH:13][CH:12]=[CH:11][C:10]=2[O:17][CH3:18])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 577175(3-Amino-2-methylphenyl)methanolHCID 117775673-Butyryl-4-chloro-8-methoxyquinoline

Product 1

HCID 11726290HCID 11726290, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 3-butyryl-4-chloro-8-methoxyquinoline (1.32 g, 5 mmol) and 3-amino-2-methylbenzyl alcohol (0.82 g, 6 mmol) in dioxan (25 ml) was heated at reflux for 1.5 hours, then the solvent evaporated. Aqueous sodium bicarbonate was added, the product extracted into dichloromethane, dried and evaporated. Recrystallisation from methanol gave 3-butyryl-4-(3-hydroxymethyl-2-methylphenylamino)-8-methoxyquinoline (1.20 g, 66%), m.p. 186°-188°.

Workup

  1. temperatureat reflux for 1.5 hours
  2. customthe solvent evaporated
  3. additionAqueous sodium bicarbonate was added
  4. extractionthe product extracted into dichloromethane
  5. customdried
  6. customevaporated
  7. customRecrystallisation from methanol

Sources & evidence

ORD record
ord-3461145e70084124b0a0988373e1f3cf
Source dataset
uspto-grants-1992_01
Patent number
US05082848

Reaction notes

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