Hydrochloric Acid → N*1*-(8-Methoxy-2-methylquinolin-4-yl)-1-phenylethane-1,2-diamine

HRID 1966540Notes

Reaction equation

HRID 1966540 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]([CH3:13])[CH:9]=[C:8]2[NH:14][CH:15]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:16]([NH2:18])=O.Cl>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]([CH3:13])[CH:9]=[C:8]2[NH:14][CH:15]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:16][NH2:18]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 594747442-(8-Methoxy-2-methylquinolin-4-ylamino)-2-phenylacetamide

Product 1

HCID 70276090N*1*-(8-Methoxy-2-methylquinolin-4-yl)-1-phenylethane-1,2-diamineYield 20.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-(8-Methoxy-2-methylquinolin-4-ylamino)-2-phenylacetamide (example 74, 430 mg, 1.33 mmole) was suspended in tetrahydrofurane (20 mL) and BH3xSMe2 (2M in tetrahydrofurane) was added dropwise. The mixture was refluxed under stirring for 1 h and then stirred at RT for 12 hrs. The content of the flask was carefully mixed with 2N HCl and refluxed for 2 hrs. The reaction mixture was alkalized and extracted with dichloromethane. The organic phases were dried and concentrated. The residue thus obtained was purified using HPLC (RP-18, eluting with water/acetonitrile) to obtain the product (12%, 83 mg). ESI-MS [M+H]+=294.1 calculated for C22H21F6N3O5=293 g/mole

Workup

  1. temperatureThe mixture was refluxed
  2. stirringstirred at RT for 12 hrs
  3. temperaturerefluxed for 2 hrs
  4. extractionextracted with dichloromethane
  5. customThe organic phases were dried
  6. concentrationconcentrated
  7. customThe residue thus obtained
  8. customwas purified
  9. washHPLC (RP-18, eluting with water/acetonitrile)

Sources & evidence

ORD record
ord-6810184406f14ff78ffcfcfbc89fc124
Source dataset
uspto-grants-2013_04
Patent number
US08420670B2

Reaction notes

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