Water → (2-Amino-5-methoxyphenyl)methanol

HRID 2118011Notes

Reaction equation

HRID 2118011 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:3]=1[C:4](O)=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:3]=1[CH2:4][OH:5]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 2779305-Methoxyanthranilic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 13756678(2-Amino-5-methoxyphenyl)methanolYield 41.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
5 °C

Procedure

2-Amino-5-methoxy-benzoic acid (2.0 g, 12 mmol) in tetrahydrofuran (20 ml) was added dropwise to an ice cooled 1 molar solution of lithium aluminium hydride (14.4 ml) in tetrahydrofuran and stirred at 5° C. for 2 hours. Water (0.5 ml) was added dropwise, followed by 2 molar aqueous sodium hydroxide solution (0.5 ml). The resulting emulsion was dried over magnesium sulphate, then filtered and evaporated under reduced pressure to give the title compound as a yellow solid (766 mg).

Workup

  1. dry with materialThe resulting emulsion was dried over magnesium sulphate
  2. filtrationfiltered
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-260f7a724ebc426ab4b76bb1e04ad833
Source dataset
uspto-grants-2008_10
Patent number
US07442795B2

Reaction notes

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