2H-1,4-benzoxazin-3(4H)-one → HCID 19077119, compound

HRID 964508Notes

Reaction equation

[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[NH:4][C:3](=O)[CH2:2]1.Cl[C:13]([CH3:21])([CH2:15][CH2:16][C:17](Cl)([CH3:19])[CH3:18])[CH3:14].[Cl-].[Al+3].[Cl-].[Cl-].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>ClCCl.C1COCC1>[CH3:18][C:17]1([CH3:19])[CH:16]=[CH:15][C:13]([CH3:21])([CH3:14])[C:8]2[C:9]1=[CH:10][C:5]1[NH:4][CH2:3][CH2:2][O:1][C:6]=1[CH:7]=2

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 6-6-9-9-tetramethyl-6,9-dihydro-4H-naphtho[2,3-b][1,4]oxazin-3-one (400 mg, 1.5 mmol) [prepared by Friedel Crafts alkylation/annulation of 2H-1,4-benzoxazin-3-(4H)-one with 2,5-dichloro-2,5-dimethyl hexane in the presence of aluminum chloride at ambient temperatue (24° C.) in dichloromethane]in THF at ambient temperature was added LiA1H4 (4.6 ml, 4.6 mmol). The reaction mixture was allowed to stir and then was heated to 80° C. for 30 min. The reaction mixture was poured over saturated sodium potassium tartrate solution (100 ml), extracted with EtOAc (100 ml), dried with anhydrous MgSO4 (0.5 g), and concentrated to give 6,6,9,9-tetramethyl-3,4,6,9-tetrahydro-2H-naphtho[2,3-b][1,4]oxazine (300 mg, 70% yield of theory): 1H NMR (400 MHz, CDCl3) δ 6.70 (s, 1H, benzylic), 6.52 (s, 1H, benzylic), 4.23 (t, 2H, J=2.8, 1.6 Hz, ring CH2), 3.39 (t, 2H, J=4.4, 6.8 Hz, ring CH2), 1.63 (s, 4H, 2 CH2), 1.22 (s, 12H, 4 CH3).

Workup

additionwas added LiA1H4 (4.6 ml, 4.6 mmol)
extractionextracted with EtOAc (100 ml)
dry with materialdried with anhydrous MgSO4 (0.5 g)
concentrationconcentrated

Sources & evidence

ORD record: ord-5de4f2853f754b9fb5ab71ab9a5e00be
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05770382

Reaction notes

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