Sodium Carbonate → HCID 86664084, compound

HRID 1615878Notes

Reaction equation

HRID 1615878 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][C:3]=1[N+:19]([O-])=O.O.O.[Sn](Cl)Cl.[NH4+].[OH-].C([O-])([O-])=O.[Na+].[Na+]>C(OCC)(=O)C>[NH2:19][C:3]1[CH:4]=[C:5]([C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:6]=[N:7][C:2]=1[Cl:1]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 14923Ammonium HydroxideHCID 61436Stannous chloride dihydrateHCID 86664083HCID 86664083, compound

Product 1

HCID 86664084HCID 86664084, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 3-(6-chloro-5-nitropyridin-3-yl)benzoate (3.0 g, 9.08 mmol) in ethyl acetate (50 mL) was added Tin(II) chloride dihydrate (11.06 g, 49.01 mmol). The reaction mixture was stirred for 10 hours at room temperature. The reaction mixture was cooled to 0° C. and then NH4OH solution was added to the reaction mixture and it was allowed to reach around pH=5 (monitored with pH paper). The reaction mixture was neutralized with Na2CO3 and the resulting white solid was filtered and washed with ether (100 mL) three times. The organic layer was concentrated to give 2.3 g (84%, yield) of ethyl 3-(5-amino-6-chloropyridin-3-yl)benzoate as a tan solid.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. filtrationthe resulting white solid was filtered
  3. washwashed with ether (100 mL) three times
  4. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-514bf9b1bf11483a86adc470db6ff5b1
Source dataset
uspto-grants-2014_07
Patent number
US08765747B2

Reaction notes

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