Sodium sulfate decahydrate → 3-Chloro-5-(hydroxymethyl)benzamide

HRID 1432064Notes

Reaction equation

HRID 1432064 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([Cl:14])[CH:13]=1)[C:7](OC)=[O:8])(=[O:3])[NH2:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[Cl:14][C:12]1[CH:13]=[C:4]([CH:5]=[C:6]([CH2:7][OH:8])[CH:11]=1)[C:1]([NH2:2])=[O:3]

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 58963003Methyl 3-carbamoyl-5-chlorobenzoate

Product 1

HCID 589629763-Chloro-5-(hydroxymethyl)benzamideYield 40.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Step N4. To above methyl 3-carbamoyl-5-chlorobenzoate (˜9.3 mmol) in dry THF (100 mL) was added lithium aluminum hydride (1 g, 26.3 mmol) in portions. The mixture was stirred for 4 hours, then treated with sodium sulfate decahydrate (8.5 g, 26.3 mmol) for 30 min. The solid was filtered off and washed with THF for three times. The solvent was removed under vacuum and resulting residue was purified by column with DCM, then MeOH/DCM (5/95) to give 3-chloro-5-(hydroxymethyl)benzamide (13, 0.7 g, 40%).

Workup

  1. filtrationThe solid was filtered off
  2. washwashed with THF for three times
  3. customThe solvent was removed under vacuum
  4. customresulting residue
  5. customwas purified by column with DCM

Sources & evidence

ORD record
ord-b345ff0a8ab64868bf750c4c9695934b
Source dataset
uspto-grants-2009_11
Patent number
US07612069B2

Reaction notes

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