Methyl Anthranilate → HCID 15922435, compound

HRID 1663067Notes

Reaction equation

HRID 1663067 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[C:5](=[CH:7][CH:8]=[CH:9][CH:10]=1)[NH2:6].[F:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCCl>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH:6][CH2:17][C:16]1[CH:19]=[CH:20][C:13]([F:12])=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 8635Methyl AnthranilateHCID 680234-FluorobenzaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 15922435HCID 15922435, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a stirred mixture of anthranilic acid methyl ester (5.0 g) and 4-fluorobenzaldehyde (3.55 ml) in 1,2-dichloroethane (50 ml) was added sodium triacetoxy-borohydride (10.5 g). The reaction mixture was stirred at room temperature for 15 hours. Saturated aqueous sodium bicarbonate was added. Layers were separated and the aqueous layer was extracted with 1,2-dichloroethane. The combined organic layers were washed with water and brine, dried (Na2SO4) and evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel (elution with EtOAc/petroleum ether 1/9) and gave 2-(4-fluoro-benzylamino)-benzoic acid methyl ester (6.22 g). The obtained ester was converted into the title compound using general procedure 2. 13C-NMR (DMSO-d6) δ 169.9, 161.1, 150.4, 135.5, 134.3, 131.6, 128.9, 115.2, 114.5, 111.6, 110.4, 45.0.

Workup

  1. customLayers were separated
  2. extractionthe aqueous layer was extracted with 1,2-dichloroethane
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a10537e5fa3d4cde9d4cf80047f2d2c8
Source dataset
uspto-grants-2011_10
Patent number
US08034811B2

Reaction notes

Loading…