Hydrochloric Acid → HCID 59286131, compound

HRID 1957964Notes

Reaction equation

HRID 1957964 reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:8]=[C:7]([NH2:15])[CH:6]=1)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl.[Cl-].[NH4+]>C1COCC1.O.C(OCC)(=O)C>[NH2:15][C:7]1[CH:6]=[C:5]([CH2:4][OH:3])[CH:10]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:8]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 61608684ethyl 3-amino-5-(methylsulfonyl)benzoate

Product 1

HCID 59286131HCID 59286131, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Amino-5-(methylsulfonyl)-benzoic acid ethyl ester (100 mg; 0.4 mmol) was dissolved in THF (4 ml), treated with lithium aluminiumhydride (33 mg; 0.9 mmol) and stirred for 18 hours at room temperature. The reaction mixture was treated in sequence with ethyl acetate (4 ml), water (0.5 ml), hydrochloric acid (5% solution in water; 0.5 ml) and a saturated aqueous ammoniumchloride solution (1.5 ml). The aqueous phase was extracted with dichloromethane and the organic phase was filtrated on a silica pad then dried and concentrated. 55 mg (0.27 mmol; 68% yield) of an orange oil were obtained.

Workup

  1. extractionThe aqueous phase was extracted with dichloromethane
  2. filtrationthe organic phase was filtrated on a silica pad
  3. customthen dried
  4. concentrationconcentrated
  5. custom55 mg (0.27 mmol; 68% yield) of an orange oil were obtained

Sources & evidence

ORD record
ord-5f719f6a6b074053b43ff79a1a4ffb61
Source dataset
uspto-grants-2013_04
Patent number
US08410100B2

Reaction notes

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