Hydrochloric Acid → 6-(Hydroxymethyl)-2H-1,4-benzoxazin-3(4H)-one

HRID 1714815Notes

Reaction equation

HRID 1714815 reaction equation
[O:1]=[C:2]1[NH:7][C:6]2[CH:8]=[C:9]([C:12](OC)=[O:13])[CH:10]=[CH:11][C:5]=2[O:4][CH2:3]1.[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1>[OH:13][CH2:12][C:9]1[CH:10]=[CH:11][C:5]2[O:4][CH2:3][C:2](=[O:1])[NH:7][C:6]=2[CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2974054Methyl 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 184524436-(Hydroxymethyl)-2H-1,4-benzoxazin-3(4H)-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

A mixture of 6.9 g of methyl 3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylate in 230 ml of tetrahydrofuran is cooled to −40° C. 88.9 ml of diisobutylaluminium hydride (1.5M in toluene) are added dropwise at −40° C. over the course of 30 minutes. The reaction mixture is stirred at −40° C. to −20° C. for 1.5 hours and then cautiously poured into 150 ml of 2N HCl (cold). The organic phase is separated off, and the aqueous phase is extracted with tetrahydrofuran (5×100 ml). The organic phases are washed with brine (1×100 ml), filtered through cotton wool and evaporated. The title compound is obtained as beige crystals from the residue by crystallization (from ethanol). Rf=0.16 (EtOAc/heptane 2.1); Rt=2.23; m.p.: 186-187° C.

Workup

  1. customThe organic phase is separated off
  2. extractionthe aqueous phase is extracted with tetrahydrofuran (5×100 ml)
  3. washThe organic phases are washed with brine (1×100 ml)
  4. filtrationfiltered through cotton wool
  5. customevaporated

Sources & evidence

ORD record
ord-4a4fccdbf71b41fb91a24d2cce84bcae
Source dataset
uspto-grants-2010_09
Patent number
US07799779B2

Reaction notes

Loading…