Hydrochloric Acid → HCID 59377940, compound

HRID 2065737Notes

Reaction equation

HRID 2065737 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([NH2:10])[C:7]([CH3:11])=[CH:6][C:5]=1[Cl:12].[BH4-].[Li+].Cl.[OH-].[Na+]>C1COCC1>[NH2:10][C:8]1[C:7]([CH3:11])=[CH:6][C:5]([Cl:12])=[C:4]([CH2:3][OH:2])[CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4148881Lithium borohydrideHCID 57423009Benzoic acid, 5-amino-2-chloro-4-methyl-, methyl ester

Product 1

HCID 59377940HCID 59377940, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-amino-2-chloro-4-methyl-benzoic acid methyl ester (0.44 g, 2.204 mmol) in THF (5 ml) was added lithium borohydride (012 g, 5.509 mmol). The mixture was heated at reflux for three hours. The mixture was cooled to 0° C., acidified with 2N aqueous HCl, and the mixture was stirred for 10 minutes. The mixture was taken to pH7 with 2N aqueous NaOH and the product was extracted with EtOAc. The combined extracts were washed with water, brine dried over MgSO4, filtered and concentrated to dryness under reduced pressure. Purification of the crude product by flash chromatography (hexanes:EtOAc 6:4) gave 0.278 g (73%) of (5-amino-2-chloro-4-methyl-phenyl)-methanol as a white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for three hours
  3. extractionthe product was extracted with EtOAc
  4. washThe combined extracts were washed with water, 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 6:4)

Sources & evidence

ORD record
ord-01819287292244a89cbb3dee5cda17f6
Source dataset
uspto-grants-2012_10
Patent number
US08288552B2

Reaction notes

Loading…