1,2-Dibromoethane → 9-(2,4-Dichloroanilino)-3,4-dihydro-2H-[1,4]oxazino[2,3-g]quinoline-8-carbonitrile

HRID 396191Notes

Reaction equation

HRID 396191 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[Cl:22])=[C:7]([C:12]#[N:13])[CH:8]=[N:9]2)=[CH:4][C:3]=1[OH:23].Br[CH2:25][CH2:26]Br.C(=O)([O-])[O-].[K+].[K+]>C(OCCO)C>[Cl:22][C:16]1[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:15]=1[NH:14][C:6]1[C:5]2[CH:4]=[C:3]3[O:23][CH2:25][CH2:26][NH:1][C:2]3=[CH:11][C:10]=2[N:9]=[CH:8][C:7]=1[C:12]#[N:13]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 230030507-Amino-4-(2,4-dichloroanilino)-6-hydroxy-3-quinolinecarbonitrile

Product 1

HCID 101772159-(2,4-Dichloroanilino)-3,4-dihydro-2H-[1,4]oxazino[2,3-g]quinoline-8-carbonitrileYield 15%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Conditions

Temperature
150 °C

Procedure

An amount of 1100 mg (3.2 mmol) of 7-amino-4-(2,4-dichloroanilino)-6-hydroxy-3-quinolinecarbonitrile was stirred in 2-ethoxyethanol (250 mL), and to this were added 1,2-dibromoethane (6.5 g, 34 mmol), and potassium carbonate (2.7 g, 19.2 mmol). The mixture was heated at 150° C. for 0.5 hours, cooled to room temperature, and filtered through a Magnesol pad. The filtrate was evaporated to a brown oil, taken up in ethyl acetate and basified with saturated sodium bicarbonate solution. After separation of the layers, the organic layer was washed with saturated brine solution, dried over sodium sulfate, and evaporated to a brown oil. Purification was carried out by flash chromatography (ethyl acetate), to give a yellow solid (175 mg, 15% yield), mp 254-255° C.; 1H NMR (DMSO-d6) δ 9.20 (s, 1H), 8.25 (s, 1H), 7.70 (dd, 2H), 7.41 (dd, 2H), 7.14 (s, 1H), 6.92 (s, 1H), 4.23 (t, 2H), 3.43 (t, 2H); I-IRMS (EI) m/z 371.04502 (M+1). Analysis for C18H12Cl2N4O.0.1CH3CO2C2H5: Found: C, 58.03; H, 3.45; N, 14.49. Calcd: C, 58.10; H, 3.37; N, 14.74.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered through a Magnesol pad
  3. customThe filtrate was evaporated to a brown oil
  4. customAfter separation of the layers
  5. washthe organic layer was washed with saturated brine solution
  6. dry with materialdried over sodium sulfate
  7. customevaporated to a brown oil
  8. customPurification

Sources & evidence

ORD record
ord-d7119322de5f42c6989331164ca2e983
Source dataset
uspto-grants-2003_08
Patent number
US06608048B2

Reaction notes

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