Hydrochloric Acid → HCID 67457791, compound

HRID 471898Notes

Reaction equation

HRID 471898 reaction equation
COC1C=CC(C[N:10]2[C:15]3[CH:16]=[C:17]([O:20][C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:19][C:14]=3[O:13][C:12]([CH3:28])([C:25]([OH:27])=[O:26])[CH2:11]2)=CC=1.[ClH:29]>CO.[OH-].[OH-].[Pd+2]>[ClH:29].[CH3:28][C:12]1([C:25]([OH:27])=[O:26])[CH2:11][NH:10][C:15]2[CH:16]=[C:17]([O:20][C:21]([F:22])([F:23])[F:24])[CH:18]=[CH:19][C:14]=2[O:13]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59395039HCID 59395039, compound

Product 1

HCID 67457791HCID 67457791, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

4-[(4-methoxyphenyl)methyl]-2-methyl-6-(trifluoromethoxy)-3H-1,4-benzoxazine-2-carboxylic acid (300 mg, 0.7550 mmol) was dissolved in methanol (50 mL) and 2 M HCl (2 mL), and treated with Pd(OH)2 under H2 (90 bar) at 100° C. (H-Cube, ThalesNano). The product solution was dried down to a brown residue. The residue was redissolved in acetonitrile, filtered and concentrated in vacuo to provide 2-methyl-6-(trifluoromethoxy)-3,4-dihydro-1,4-benzoxazine-2-carboxylic acid hydrochloride (200 mg, 85% yield) as a brown solid. LC/MS m/z 278.3 [M+H]+.

Workup

  1. customThe product solution was dried down to a brown residue
  2. dissolutionThe residue was redissolved in acetonitrile
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d3beb476c59445cd93d07c6d1459ba5d
Source dataset
uspto-grants-2014_01
Patent number
US08633189B2

Reaction notes

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