Dimethylformamide → HCID 18957888, compound

HRID 2379122Notes

Reaction equation

HRID 2379122 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.O.[NH2:12][C:13]1[CH:14]=[C:15]([B:19]([OH:21])[OH:20])[CH:16]=[CH:17][CH:18]=1.[C:22](=O)([O-])[O-:23].[Na+].[Na+].CN(C=O)C>C(OCC)(=O)C>[N+:8]([C:7]1[C:2]([N:12]([CH:22]=[O:23])[C:13]2[CH:14]=[C:15]([B:19]([OH:21])[OH:20])[CH:16]=[CH:17][CH:18]=2)=[N:3][CH:4]=[CH:5][CH:6]=1)([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 796132-Chloro-3-nitropyridineHCID 143894233-Aminophenylboronic acid monohydrate

Product 1

HCID 18957888HCID 18957888, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

. A mixture of 2-chloro-3-nitropyridine (5.0 g, 32.2 mmol), 3-aminophenylboronic acid monohydrate (5.11 g, 32.2 mmol), sodium carbonate (13.7 g, 32.2 mmol), and DMF (100 ml) was stirred at 100° C. for 1 h. After cooling to room temperature, ethyl acetate (500 ml) was added and the solids were filtered off. The solution was transferred to a separatory funnel and washed with aqueous hydrochloric acid (3×200 ml, 1M). The organic phase was dried and the solvent removed. Yield 6.5 g, mp 242°-245° C.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe solids were filtered off
  3. customThe solution was transferred to a separatory funnel
  4. washwashed with aqueous hydrochloric acid (3×200 ml, 1M)
  5. customThe organic phase was dried
  6. customthe solvent removed

Sources & evidence

ORD record
ord-8c3606f24adf4debbc2facd27de717d6
Source dataset
uspto-grants-1994_11
Patent number
US05360809

Reaction notes

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