Cesium carbonate → Ammonium Hydroxide

HRID 1925354Notes

Reaction equation

HRID 1925354 reaction equation
[O:1]1[CH2:6][CH2:5][NH:4][C:3]2[CH:7]=[CH:8][C:9]([OH:11])=[CH:10][C:2]1=2.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:19]1[C:28]2[C:23](=[CH:24][C:25]([O:31][CH3:32])=[C:26]([O:29][CH3:30])[CH:27]=2)[N:22]=[CH:21][CH:20]=1>CN(C=O)C>[NH4+:4].[OH-:1].[CH3:30][O:29][C:26]1[CH:27]=[C:28]2[C:23](=[CH:24][C:25]=1[O:31][CH3:32])[N:22]=[CH:21][CH:20]=[C:19]2[O:11][C:9]1[CH:8]=[CH:7][C:3]2[NH:4][CH2:5][CH2:6][O:1][C:2]=2[CH:10]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 193865643,4-dihydro-2H-benzo[b][1,4]oxazin-7-ol

Product 2

HCID 14923Ammonium HydroxideHCID 248240487-(6,7-dimethoxyquinolin-4-yloxy)-3,4-dihydro-2H-benzo[b][1,4]oxazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3,4-dihydro-2H-benzo[b][1,4]oxazin-7-ol (2.5 g, 16.54 mmol), cesium carbonate (16.167, 49.62 mmol), and 4-chloro-6,7-dimethoxyquinoline (5.534 g, 24.81 mmol) in DMF (30 mL) was stirred for 15 h at 80° C. The solution was concentrated in vacuo and purified with column chromatography using 100% CH2Cl2→10% 90:10:1 CH2Cl2:MeOH:NH4OH to yield the title compound. MS (ESI, pos. ion) m/z: 339 (M+1). Mass calc'd for C19H18N2O4: 338.13.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. custompurified with column chromatography

Sources & evidence

ORD record
ord-7f5d5d2241cf4a179788710cf1e9620b
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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