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

HRID 2246910Notes

Reaction equation

HRID 2246910 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[O:13][CH2:12][C:11](=[O:14])[NH:10][C:9]=2[CH:15]=1)=O.[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1>[OH:2][CH2:3][C:5]1[CH:6]=[CH:7][C:8]2[O:13][CH2:12][C:11](=[O:14])[NH:10][C:9]=2[CH:15]=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

Procedure

To a mixture of 6.9 g of 3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-carboxylic acid methyl ester [604756-32-3] in 230 ml of tetrahydrofuran are added 88.9 ml of diisobutylaluminiumhydride (1.5M in toluene) at −40° C. The reaction mixture is stirred for 1.5 hours at −40° C. to −20° C. and poured into 150 ml of 2N hydrochloric acid. The organic phase is separated, washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The residue is crystallized from ethanol to afford the title compound as a beige solid. Rf=0.16 (EtOAc-heptan 2:1); Rt=2.23, m.p.: 186-187° C.

Workup

  1. customThe organic phase is separated
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is crystallized from ethanol

Sources & evidence

ORD record
ord-47413430f70b4e0ca718ea7c58a0e937
Source dataset
uspto-grants-2010_03
Patent number
US07687495B2

Reaction notes

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