HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Potassium Carbonate → Tert-butyl {4-[(3-amino-7-bromoquinolin-4-ylamino)methyl]benzyl}carbamate

HRID 9490
Notes
Print preview

Reaction equation

HRID 9490 reaction equation
C(=O)([O-])[O-].[K+].[K+].S(S([O-])=O)([O-])=O.[Na+].[Na+].[C:15]([O:19][C:20](=[O:45])[NH:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][NH:30][C:31]2[C:40]3[C:35](=[CH:36][C:37]([Br:41])=[CH:38][CH:39]=3)[N:34]=[CH:33][C:32]=2[N+:42]([O-])=O)=[CH:25][CH:24]=1)([CH3:18])([CH3:17])[CH3:16]>O.ClCCl.CC[N+]1C=CC(C2C=C[N+](CC)=CC=2)=CC=1.[Br-].[Br-]>[C:15]([O:19][C:20](=[O:45])[NH:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][NH:30][C:31]2[C:40]3[C:35](=[CH:36][C:37]([Br:41])=[CH:38][CH:39]=3)[N:34]=[CH:33][C:32]=2[NH2:42])=[CH:25][CH:24]=1)([CH3:18])([CH3:16])[CH3:17]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 24489Sodium DithioniteHCID 21984421Tert-butyl {4-[(7-bromo-3-nitroquinolin-4-ylamino)methyl]benzyl}carbamate

Product 1

HCID 21984367Tert-butyl {4-[(3-amino-7-bromoquinolin-4-ylamino)methyl]benzyl}carbamateYield 100.5%

Reagents, catalysts & solvents 3

HCID 11474262
1,1'-Diethyl-4,4'-bipyridinium dibromide
Catalyst
HCID 962WaterSolvent3×
HCID 6344DichloromethaneSolvent2×

Procedure

Ethyl viologen dibromide (0.069 g, 0.18 mmol), potassium carbonate (12.76 g, 92 mmol) in water (55mL), and sodium hydrosulfite (11.25 g, 65 mmol) in water (55mL) were added sequentially to a solution of tert-butyl{4-[(7-bromo-3-nitroquinolin-4-ylamino)methyl]benzyl}carbamate (9.0 g, 18.5 mmol) in dichloromethane (110 mL). The resulting biphasic mixture was stirred for 20 hours. The reaction was diluted with water (600 mL) and dichloromethane (500 mL). The layers were separated and the aqueous fraction was extracted with dichloromethane. The organic fractions were combined and washed sequentially with water and saturated aqueous sodium chloride. The organic fraction was dried over sodium sulfate, filtered, and concentrated under reduced pressure to yield 8.5 g of tert-butyl{4-[(3-amino-7-bromoquinolin-4-ylamino)methyl]benzyl}carbamate as a yellow-brown amorphous solid.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous fraction was extracted with dichloromethane
  3. washwashed sequentially with water and saturated aqueous sodium chloride
  4. dry with materialThe organic fraction was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e14b4f690e7d423e92497dc07775b581
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07091214B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes