Hydrochloric Acid → 8-{2-[2-(3,5-dimethylphenyl)-1,1-dimethylethylamino]-1-hydroxyethyl}-6-hydroxy-4H-benzo[1,4]oxazin-3-one

HRID 12112Notes

Reaction equation

HRID 12112 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:20]([OH:35])[CH2:21][NH:22][C:23]([CH3:34])([CH3:33])[CH2:24][C:25]2[CH:30]=[C:29]([CH3:31])[CH:28]=[C:27]([CH3:32])[CH:26]=2)[C:12]2[O:17][CH2:16][C:15](=[O:18])[NH:14][C:13]=2[CH:19]=1)C1C=CC=CC=1.Cl>C(O)(C)C>[CH3:32][C:27]1[CH:26]=[C:25]([CH2:24][C:23]([NH:22][CH2:21][CH:20]([C:11]2[C:12]3[O:17][CH2:16][C:15](=[O:18])[NH:14][C:13]=3[CH:19]=[C:9]([OH:8])[CH:10]=2)[OH:35])([CH3:34])[CH3:33])[CH:30]=[C:29]([CH3:31])[CH:28]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 220634496-benzyloxy-8-{2-[2-(3,5-dimethylphenyl)-1,1-dimethylethylamino]-1-hydroxyethyl}-4H-benzo[1,4]oxazin-3-one

Product 1

HCID 115745358-{2-[2-(3,5-dimethylphenyl)-1,1-dimethylethylamino]-1-hydroxyethyl}-6-hydroxy-4H-benzo[1,4]oxazin-3-one

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The target compound was obtained after hydrogenolysis of 0.90 g (1.71 mmol) of 6-benzyloxy-8-{2-[2-(3,5-dimethylphenyl)-1,1-dimethylethylamino]-1-hydroxyethyl}-4H-benzo[1,4]oxazin-3-one and recrystallization of the crude product from isopropanol. White solid. Yield: 0.50 g (69%, hydrochloride); melting point: 235° C.-238° C.; mass spectroscopy: [M+H]+=385.

Workup

  1. customThe target compound was obtained

Sources & evidence

ORD record
ord-5f64649a2d3343dca5f41288ea2360de
Source dataset
uspto-grants-2010_06
Patent number
US07727984B2

Reaction notes

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