tert-Butyl [2-(6-acetyl-4-chloro-2-formyl-3-methylphenoxy)ethyl]carbamate → 1-(7-Chloro-6-methyl-2,3-dihydro-1,4-benzoxazepin-9-yl)ethanone

HRID 626816Notes

Reaction equation

HRID 626816 reaction equation
[C:1]([C:4]1[C:9]([O:10][CH2:11][CH2:12][NH:13]C(=O)OC(C)(C)C)=[C:8]([CH:21]=O)[C:7]([CH3:23])=[C:6]([Cl:24])[CH:5]=1)(=[O:3])[CH3:2]>Cl.O1CCOCC1>[Cl:24][C:6]1[CH:5]=[C:4]([C:1](=[O:3])[CH3:2])[C:9]2[O:10][CH2:11][CH2:12][N:13]=[CH:21][C:8]=2[C:7]=1[CH3:23]

Participants

4

Reactant 1

HCID 86697512tert-Butyl [2-(6-acetyl-4-chloro-2-formyl-3-methylphenoxy)ethyl]carbamate

Product 1

HCID 866975131-(7-Chloro-6-methyl-2,3-dihydro-1,4-benzoxazepin-9-yl)ethanoneYield 100%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl [2-(6-acetyl-4-chloro-2-formyl-3-methylphenoxy)ethyl]carbamate (270 mg, 0.76 mmol) was stirred in 4.0 M hydrogen chloride in dioxane (5.0 mL) at room temperature for 1 hour and evaporated. Tetrahydrofuran was added and the mixture was evaporated to give the desired compound (180 mg, 100%). LCMS calculated for C12H13ClNO2 (M+H)+: m/z=238.1; found: 238.0.

Workup

  1. customevaporated
  2. additionTetrahydrofuran was added
  3. customthe mixture was evaporated

Sources & evidence

ORD record
ord-94af0f3fb8c54289860e311e2655cc77
Source dataset
uspto-grants-2016_04
Patent number
US09309251B2

Reaction notes

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