1,2-Dichloroethane → Phenylmethyl 3-amino-4-methoxybenzoate

HRID 1776539Notes

Reaction equation

HRID 1776539 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([OH:7])=[O:6].[C:13]1([CH2:19]O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(Cl)CCl>CN(C1C=CN=CC=1)C.CN(C=O)C>[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([O:7][CH2:19][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:6]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 244Benzyl AlcoholHCID 178233-Amino-4-methoxybenzoic acid

Product 1

HCID 54195745Phenylmethyl 3-amino-4-methoxybenzoateYield 52%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

3-amino-4-methoxybenzoic acid (20 g, 120 mmol), phenylmethanol (12.94 g, 120 mmol), DMAP (14.62 g, 120 mmol), and EDC (22.94 g, 120 mmol) were dissolved in DMF (100 ml). The reaction was stirred at RT for 2 hours. The reaction mixture was filtered, and the mother liquor was diluted with water and extracted with EtOAc. The organic phase was extracted with water, dried over Na2SO4 and evaporated under vacuum. The crude product was crystallized in EtOAc. The mother liquor are purified by flash chromatography (Petroleum Ether/EtOAc 80/20). The overall amount of the desired product was 16 g (Yield: 52%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. additionthe mother liquor was diluted with water
  3. extractionextracted with EtOAc
  4. extractionThe organic phase was extracted with water
  5. dry with materialdried over Na2SO4
  6. customevaporated under vacuum
  7. customThe crude product was crystallized in EtOAc
  8. customThe mother liquor are purified by flash chromatography (Petroleum Ether/EtOAc 80/20)

Sources & evidence

ORD record
ord-99caeb0deeeb494fa8916ecc0d29ad34
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

Loading…