2-Amino-6-methoxybenzoic Acid → (2-Amino-6-methoxyphenyl)methanol

HRID 1497742Notes

Reaction equation

HRID 1497742 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH2:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[C:9]=1[C:10](O)=[O:11]>C1COCC1>[NH2:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[C:9]=1[CH2:10][OH:11]

Participants

4

Reactant 2

HCID 27353572-Amino-6-methoxybenzoic AcidHCID 21226445Aluminium lithium hydride

Product 1

HCID 45090906(2-Amino-6-methoxyphenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of LiAlH4 (6.826 g, 0.018 mol) and THF (300 mL) is stirred at 0° C. 2-amino-6-methoxy-benzoic acid (15 g, 0.09 mol) in THF (150 mL) is added to the reaction mixture. The mixture is stirred at room temperature for 3 h. The reaction is quenched by the addition of water. 250 mL of 10% NaOH solution is then added and extracted from water with ethylacetate to give the desired product.

Workup

  1. stirringThe mixture is stirred at room temperature for 3 h
  2. customThe reaction is quenched by the addition of water
  3. addition250 mL of 10% NaOH solution is then added
  4. extractionextracted from water with ethylacetate

Sources & evidence

ORD record
ord-c972792559e349de9a8d5ef44a3a004d
Source dataset
uspto-grants-2015_12
Patent number
US09199988B2

Reaction notes

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