Hydrochloric Acid → HCID 59377969, compound

HRID 2065742Notes

Reaction equation

HRID 2065742 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1[CH:11]=[C:10]([NH2:12])[C:9]([CH3:13])=[CH:8][C:7]=1[Cl:14])C.[BH4-].[Li+].Cl.[OH-].[Na+]>C1COCC1>[NH2:12][C:10]1[C:9]([CH3:13])=[CH:8][C:7]([Cl:14])=[C:6]([CH2:5][CH2:4][OH:3])[CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4148881Lithium borohydrideHCID 59378012HCID 59378012, compound

Product 1

HCID 59377969HCID 59377969, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (5-amino-2-chloro-4-methyl-phenyl)-acetic acid ethyl ester (0.25 g, 1.09 mmol) in THF (15 ml) was added lithium borohydride (0.059 g, 2.74 mmol) and the mixture was heated at reflux for three hours. The mixture was cooled to 0° C. and acidified to pH 1 with aqueous 2N HCl. The mixture was taken to pH7 by addition of aqueous 2N NaOH and the mixture was extracted with EtOAc. The combined extracts were washed with water and brine dried, over MgSO4, filtered and concentrated to dryness under reduced pressure. Purification of the crude product by flash chromatography (hexanes:EtOAc 1:1) gave 0.203 g (99%) of 2-(5-amino-2-chloro-4-methyl-phenyl)-ethanol as a white solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for three hours
  3. extractionthe mixture was extracted with EtOAc
  4. washThe combined extracts were washed with water and brine
  5. dry with materialdried, over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure
  8. customPurification of the crude product by flash chromatography (hexanes:EtOAc 1:1)

Sources & evidence

ORD record
ord-8fb41d0be7204332be72ec580b60705c
Source dataset
uspto-grants-2012_10
Patent number
US08288552B2

Reaction notes

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