4,6-Dichloro-2,3-dimethylquinoline → 4-(6-chloro-2,3-dimethyl-4-quinolinyl)-6-(4-morpholinyl)-3,4-dihydro-2H-1,4-benzoxazine

HRID 1618596Notes

Reaction equation

HRID 1618596 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:16]=[CH:15][C:10]3[O:11][CH2:12][CH2:13][NH:14][C:9]=3[CH:8]=2)[CH2:3][CH2:2]1.Cl[C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([Cl:28])[CH:26]=2)[N:21]=[C:20]([CH3:29])[C:19]=1[CH3:30]>>[Cl:28][C:25]1[CH:26]=[C:27]2[C:22](=[CH:23][CH:24]=1)[N:21]=[C:20]([CH3:29])[C:19]([CH3:30])=[C:18]2[N:14]1[C:9]2[CH:8]=[C:7]([N:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)[CH:16]=[CH:15][C:10]=2[O:11][CH2:12][CH2:13]1

Participants

3

Reactant 2

HCID 609949634,6-Dichloro-2,3-dimethylquinolineHCID 67285003HCID 67285003, compound

Product 1

HCID 509403334-(6-chloro-2,3-dimethyl-4-quinolinyl)-6-(4-morpholinyl)-3,4-dihydro-2H-1,4-benzoxazine

Procedure

Prepared according to procedure T using 6-morpholino-3,4-dihydro-2H-benzo-[b][1,4]oxazine (0.1 g, 0.454 mmol) and 4,6-dichloro-2,3-dimethylquinoline (0.2053 g, 0.908 mmol) to give 4-(6-chloro-2,3-dimethyl-4-quinolinyl)-6-(4-morpholinyl)-3,4-dihydro-2H-1,4-benzoxazine as a yellow solid: 1H NMR (500 MHz, DMSO-d6) δ ppm 8.01 (1H, d, J=9.5 Hz), 7.64-7.73 (2H, m), 6.77 (1H, d, J=8.6 Hz), 6.22 (1H, dd, J=8.7, 2.6 Hz), 5.41 (1H, d, J=2.7 Hz), 4.26-4.47 (2H, m), 3.57-3.67 (2H, m), 3.47-3.55 (4H, m), 2.69 (3H, s), 2.60-2.66 (4H, m), 2.22 (3H, s); Mass Spectrum (ESI) m/e=410.2 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-7826efe84f004b4e8d2d0ac52843177d
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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