Hydrochloric Acid → methyl N-(2-chloro-5-hydroxymethylbenzyl)carbamate

HRID 2414261Notes

Reaction equation

HRID 2414261 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](OC)=[O:7])=[CH:4][C:3]=1[CH2:12][NH:13][C:14]([O:16][CH3:17])=[O:15].[H-].C([Al+]CC(C)C)C(C)C.Cl.O>O1CCCC1>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[CH2:12][NH:13][C:14](=[O:15])[O:16][CH3:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 21225700DiisobutylaluminumhydrideHCID 22645128Methyl 4-chloro-3-(methoxycarbonylaminomethyl)benzoate

Product 1

HCID 22645125methyl N-(2-chloro-5-hydroxymethylbenzyl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

10.3 g of methyl 4-chloro-3-(methoxycarbonylaminomethyl)benzoate was dissolved in 80 ml of anhydrous tetrahydrofuran, 100 ml of diisobutylaluminum hydride (0.95 M hexane solution) was dropwise added thereto in an atmosphere of nitrogen at from −50° C. to −30° C., and after completion of the dropwise addition, the mixture was stirred at room temperature for 16 hours. After completion of the reaction, diluted hydrochloric acid was dropwise added to the reaction mixture at 0° C., water was added thereto, extraction with ethyl acetate was carried out, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (Wakogel C-200, eluent: hexane/ethyl acetate=1/1) to obtain 6.5 .g of methyl N-(2-chloro-5-hydroxymethylbenzyl)carbamate as white crystals.

Workup

  1. additionin an atmosphere of nitrogen at from −50° C. to −30° C., and after completion of the dropwise addition
  2. additionwas dropwise added to the reaction mixture at 0° C.
  3. extractionextraction with ethyl acetate
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (Wakogel C-200, eluent: hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-87494c210889426a80febecca381016e
Source dataset
uspto-grants-2004_11
Patent number
US06812229B1

Reaction notes

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