Dichloromethane → HCID 57447056, compound

HRID 2366663Notes

Reaction equation

HRID 2366663 reaction equation
[CH3:1][C:2]([CH3:23])([CH2:8][NH:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=[CH:12][C:11]=1[N+:20]([O-])=O)[C:3]([O:5][CH2:6][CH3:7])=[O:4].S(S([O-])=O)([O-])=O.[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+].ClCCl>CC[N+]1C=CC(C2C=C[N+](CC)=CC=2)=CC=1.[Br-].[Br-].O>[NH2:20][C:11]1[CH:12]=[N:13][C:14]2[C:19]([C:10]=1[NH:9][CH2:8][C:2]([CH3:1])([CH3:23])[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:18][CH:17]=[CH:16][CH:15]=2

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 24489Sodium DithioniteHCID 57447055HCID 57447055, compound

Product 1

HCID 57447056HCID 57447056, compoundYield 86.3%

Reagents, catalysts & solvents 2

HCID 114742621,1'-Diethyl-4,4'-bipyridinium dibromideCatalystHCID 962WaterSolvent

Procedure

Part D A mixture of ethyl 2,2-dimethyl-3-[(3-nitroquinolin-4-yl)amino]propanoate (59 g), sodium hydrosulfite (109 g, 532 mmol), potassium carbonate (103 g, 744 mmol), and ethyl viologen dibromide (0.50 g, 1.3 mmol), dichloromethane (350 mL), and water (350 mL) was stirred overnight at ambient temperature. The aqueous layer was separated and extracted with dichloromethane (100 mL). The combined organic fractions were washes with water (4×75 mL), dried over potassium carbonate, filtered, and concentrated under reduced pressure to provide 46.1 g of ethyl 3-[(3-aminoquinolin-4-yl)amino]-2,2-dimethylpropanoate as a dark oil. Part E

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with dichloromethane (100 mL)
  3. dry with materialdried over potassium carbonate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-42143018f4c94c41945d5ec0228c68b4
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

Loading…