Ethanol → HCID 68661711, compound

HRID 1260862Notes

Reaction equation

HRID 1260862 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12]([NH:14][CH3:15])=[O:13])[CH:11]=1)[C:5](OC)=[O:6].C(O)C.[BH4-].[Li+]>O1CCCC1>[Cl:1][C:2]1[CH:11]=[C:10]([CH:9]=[C:4]([CH2:5][OH:6])[CH:3]=1)[C:12]([NH:14][CH3:15])=[O:13]

Participants

5

Reactant 3

HCID 702EthanolHCID 4148881Lithium borohydrideHCID 68661921HCID 68661921, compound

Product 1

HCID 68661711HCID 68661711, compoundYield 54.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

(Step 1) To a mixed solution of methyl 3-chloro-5-[(methylamino)carbonyl]benzoate (2.5 g) in tetrahydrofuran:ethanol=10:1 (110 ml) was added lithium tetrahydroborate (0.36 g) at room temperature. After stirring at 60° C. for 4 hr, the reaction solution was quenched with ice and extracted with ethyl acetate. The extract was washed with 1N hydrochloric acid and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was treated by silica gel chromatography (ethyl acetate) to give 3-chloro-5-(hydroxymethyl)-N-methylbenzamide (1.2 g).

Workup

  1. customthe reaction solution was quenched with ice
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with 1N hydrochloric acid
  4. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. additionthe obtained residue was treated by silica gel chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-fcbda64d44124af7991cc66dcba6b3f7
Source dataset
uspto-grants-2013_06
Patent number
US08470859B2

Reaction notes

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