Methyl Anthranilate → trans-1-(2-Methoxycarbonylanilino)-2-ethoxycarbonylaminoindane

HRID 1381069Notes

Reaction equation

HRID 1381069 reaction equation
Cl[C@@H:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@H:3]1[NH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].[C:17]([O:26][CH3:27])(=[O:25])[C:18]1[C:19](=[CH:21][CH:22]=[CH:23][CH:24]=1)[NH2:20]>CCOCC>[CH3:27][O:26][C:17]([C:18]1[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=1[NH:20][C@@H:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@H:3]1[NH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:25]

Participants

4

Reactant 2

HCID 8635Methyl AnthranilateHCID 7070371trans-1-Chloro-2-ethoxycarbonylaminoindane

Product 1

HCID 54064549trans-1-(2-Methoxycarbonylanilino)-2-ethoxycarbonylaminoindaneYield 58%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

trans-1-Chloro-2-ethoxycarbonylaminoindane (20 g, 0.084 moles) was treated with methyl anthranilate (60 ml) and stirred under nitrogen at 60° for 5 hr. The resulting viscous mixture was diluted with ether (500 ml), washed exhaustively with 2.5N HCl (8×250 ml), and then with saturated sodium bicarbonate followed by brine. After drying (Na2SO4) and concentration in vacuo a brown solid (25.7 g) was obtained. Crystallisation from pentane/ether afforded the title compound (14 g; 58%) m.p. 108°-110°. Concentration of mother liquors gave a less pure second crop (2.6 g).

Workup

  1. washwashed exhaustively with 2.5N HCl (8×250 ml)
  2. customAfter drying
  3. concentration(Na2SO4) and concentration in vacuo a brown solid (25.7 g)
  4. customwas obtained
  5. customCrystallisation from pentane/ether

Sources & evidence

ORD record
ord-afcb163e608f448fb2bb3e796686dad3
Source dataset
uspto-grants-1986_04
Patent number
US04585588

Reaction notes

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