Water → HCID 69507133, compound

HRID 1623130Notes

Reaction equation

HRID 1623130 reaction equation
O.S(S([O-])=O)([O-])=O.[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+].[Br:16][C:17]1[CH:26]=[C:25]2[C:20]([C:21]([NH:30][CH2:31][CH2:32][CH2:33][CH:34]([O:37][CH3:38])[O:35][CH3:36])=[C:22]([N+:27]([O-])=O)[CH:23]=[N:24]2)=[CH:19][CH:18]=1>ClCCl.CC[N+]1C=CC(C2C=C[N+](CC)=CC=2)=CC=1.[Br-].[Br-]>[Br:16][C:17]1[CH:26]=[C:25]2[C:20]([C:21]([NH:30][CH2:31][CH2:32][CH2:33][CH:34]([O:37][CH3:38])[O:35][CH3:36])=[C:22]([NH2:27])[CH:23]=[N:24]2)=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 24489Sodium DithioniteHCID 57455396HCID 57455396, compound

Product 1

HCID 69507133HCID 69507133, compound

Reagents, catalysts & solvents 2

HCID 114742621,1'-Diethyl-4,4'-bipyridinium dibromideCatalystHCID 6344DichloromethaneSolvent

Procedure

Water (200 mL), sodium hydrosulfite (90.9 g, 522.3 mmol), ethyl viologen dibromide (0.64 g, 1.74 mL mmol) and potassium carbonate (95.0 g, 687 mmol) were sequentially added to a solution of (7-bromo-3-nitroquinolin-4-yl)(4,4-dimethoxybutyl)amine in dichloromethane and stirred overnight at ambient temperature. The layers were separated and the organic layer was washed sequentially with water (5×200 mL), saturated aqueous sodium bicarbonate, and brine, dried over magnesium sulfate, and concentrated under reduced pressure to afford 59.3 g of 7-bromo-N4-(4,4-dimethoxybutyl)quinoline-3,4 diamine as a brown oil.

Workup

  1. customThe layers were separated
  2. washthe organic layer was washed sequentially with water (5×200 mL), saturated aqueous sodium bicarbonate, and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c1d66cce282e4bbd87bb8b066b0b73e2
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

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