Benzyl Alcohol → Benzyl anthranilate

HRID 1742580

Reaction equation

HRID 1742580 reaction equation
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6][C:5](=O)[O:4][C:2]2=[O:3].C(O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CN(C)C=O.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C(OCC)(=O)C.C(Cl)Cl>[NH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:1]=1[C:2]([O:4][CH2:5][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:3]

Participants

8

Reactant 4

HCID 244Benzyl AlcoholHCID 6228DimethylformamideHCID 8359Isatoic AnhydrideHCID 8471Triethylamine

Product 1

HCID 522771Benzyl anthranilate

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of isatoic anhydride (8.54 g), benzyl alcohol (6.0 g), 4-dimethylaminopyridine (6.7 g), dimethylformamide (17 ml), triethylamine (5.28 g), and methylene chloride (160 ml) is refluxed overnight, diluted with an equal volume of ethyl acetate and washed with water, brine, and water. The organic solution is dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude product is purified by flash chromatography eluting with 30% ethyl acetate in hexane to give the desired product.

Workup

  1. temperatureis refluxed overnight
  2. washwashed with water, brine, and water
  3. dry with materialThe organic solution is dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product is purified by flash chromatography
  7. washeluting with 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-5b7fd9a50c3f42d58fe6793f43f34b9b
Source dataset
uspto-grants-1994_08
Patent number
US05340801

Linked notes

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