Sodium Bicarbonate → HCID 57652724, compound

HRID 1013265Notes

Reaction equation

HRID 1013265 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH3:21])[CH:8]=[C:9]([N+:11]([O-])=O)[CH:10]=1)=[O:4].C([O-])(O)=O.[Na+]>CCOC(C)=O>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH3:21])[CH:8]=[C:9]([NH2:11])[CH:10]=1)=[O:4]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 57652728HCID 57652728, compound

Product 1

HCID 57652724HCID 57652724, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2′-Methoxy-5-nitro-biphenyl-3-carboxylic acid methyl ester (8.2 g, 28.5 mmol) and SnCl2 dihydrate (35 g) in EtOAc (300 mL) was heated to reflux and stirred for 18 hours, then cooled and stirred at room temperature for 48 hours. Saturated aqueous NaHCO3 was added until the aqueous portion of the mixture reached pH 10. The organic layer was separated, and the aqueous layer was washed with EtOAc. The combined organic layers were washed with water, dried over Na2SO4, filtered and concentrated under reduced pressure to give 7.2 g of 5-amino-2′-methoxy-biphenyl-3-carboxylic acid methyl ester, MS (M+H)=258.

Workup

  1. temperatureto reflux
  2. temperaturecooled
  3. stirringstirred at room temperature for 48 hours
  4. customThe organic layer was separated
  5. washthe aqueous layer was washed with EtOAc
  6. washThe combined organic layers were washed with water
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9815b4a2e78f4c69937cb6436ffa99ee
Source dataset
uspto-grants-2011_07
Patent number
US07981914B2

Reaction notes

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