Ethyl 4-amino-5-chloro-2-methoxybenzoate → (4-Amino-5-chloro-2-methoxyphenyl)methanol

HRID 630384Notes

Reaction equation

HRID 630384 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]1[C:18]([Cl:19])=[CH:17][C:11]([C:12](OCC)=[O:13])=[C:10]([O:20][CH3:21])[CH:9]=1>O1CCCC1>[NH2:7][C:8]1[C:18]([Cl:19])=[CH:17][C:11]([CH2:12][OH:13])=[C:10]([O:20][CH3:21])[CH:9]=1

Participants

4

Reactant 2

HCID 732631Ethyl 4-amino-5-chloro-2-methoxybenzoate2×HCID 21226445Aluminium lithium hydride

Product 1

HCID 55277042(4-Amino-5-chloro-2-methoxyphenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of lithium aluminium hydride (0.96 g, 0.025 mol) in tetrahydrofuran (100 mL) was added dropwise at room temperature a solution of ethyl 4-amino-5-chloro-2-methoxybenzoate (intermediate 37; 4.4 g, 0.019 mol) in tetrahydrofuran (25 mL). Then the mixture was refluxed for 2 hours. The excess of hydride was destroyed by successive addition of 1 ml of water, 1 ml of 4N NaOH solution and 2 ml of water, filtered through celite and washed with ethyl acetate. The organic solvent was reduced and hexane was added. The mixture was cooled at 0° C. during 1 hour and then the precipitate was filtrated and washed with hexane. The title compound was obtained as a pale yellow solid (80%) which was used in the next step without further purification.

Workup

  1. temperatureThen the mixture was refluxed for 2 hours
  2. customThe excess of hydride was destroyed by successive addition of 1 ml of water, 1 ml of 4N NaOH solution and 2 ml of water
  3. filtrationfiltered through celite
  4. washwashed with ethyl acetate
  5. additionhexane was added
  6. filtrationthe precipitate was filtrated
  7. washwashed with hexane

Sources & evidence

ORD record
ord-f7d74ff299224c7a94569737a205dafe
Source dataset
uspto-grants-2016_04
Patent number
US09315463B2

Reaction notes

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