Hydrochloric Acid → HCID 18321969, compound

HRID 1871156Notes

Reaction equation

HRID 1871156 reaction equation
[Cl:1][C:2]1[C:20]([NH:21][C:22](=O)[CH2:23][NH2:24])=[CH:19][CH:18]=[C:17]([Cl:26])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH3:16])[CH:12]=[CH:11]2.Cl.C(=O)(O)[O-].[Na+]>O1CCCC1>[NH2:24][CH2:23][CH2:22][NH:21][C:20]1[C:2]([Cl:1])=[C:3]([C:17]([Cl:26])=[CH:18][CH:19]=1)[CH2:4][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH3:16])[CH:12]=[CH:11]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 10596531HCID 10596531, compound

Product 1

HCID 18321969HCID 18321969, compoundYield 25.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 8-[2,6-dichloro-3-glycylaminobenzyloxy]-2-methylquinoline (2.14 g) in tetrahydrofuran (21 ml) was dropwise added 2M borane-methylsulfide complex in tetrahydrofuran (5.48 ml) at 0° C. under nitrogen atmosphere, and the mixture was stirred for 15 minutes at the same temperature and refluxed for 6 hours. After cooling, the mixture was adjusted to pH 1 with 1N-hydrochloric acid and refluxed for 30 minutes. The mixture was neutralized with saturated sodium bicarbonate solution and extracted with chloroform. The extract was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by flash chromatography (chloroform) to give 8-[3-[N-(2-aminoethyl)amino]-2,6-dichlorobenzyloxy]-2-methylquinoline (525 mg) as colorless amorphous.

Workup

  1. customat 0° C.
  2. temperaturerefluxed for 6 hours
  3. temperatureAfter cooling
  4. temperaturerefluxed for 30 minutes
  5. extractionextracted with chloroform
  6. washThe extract was washed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo
  9. customThe residue was purified by flash chromatography (chloroform)

Sources & evidence

ORD record
ord-525d800a1de644e99faed6638399eaf0
Source dataset
uspto-grants-2000_08
Patent number
US06100284

Reaction notes

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