Toluene → HCID 71766905, compound

HRID 1771408Notes

Reaction equation

HRID 1771408 reaction equation
[CH2:1]([NH2:4])[CH2:2][NH2:3].C[Al](C)C.[C:9]1([CH3:15])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.BrC1C=[C:25]2C([CH2:21][CH2:22][O:23][CH:24]2C(OC)=O)=CC=1>C(Cl)Cl.CO.O>[CH3:15][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:10]=1[CH2:21][CH2:22][O:23][CH:24]2[C:25]1[NH:3][CH2:2][CH2:1][N:4]=1

Participants

8

Reactant 4

HCID 1140Toluene2×HCID 3301EthylenediamineHCID 16682925TrimethylaluminumHCID 117925509HCID 117925509, compound

Product 1

HCID 71766905HCID 71766905, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To 10 minutes ice-bath cooled and stirred solution of ethylenediamine (0.29 ml), trimethylaluminum (2M heptane sol, 2.2 ml) and toluene (10 ml) was added the mixture of methyl 7-bromoisochroman-1-carboxylate (0.5 g) and toluene (10 ml) and the reaction mixture was refluxed for 6 hrs. Water (2 ml), methanol (5 ml) and DCM (5 ml) were added, mixture refluxed for 15 min and participate was filtered off. Organics were evaporated and the title compound (0.38 g) was isolated with the separation method D (2-methoxy-2-methylpropane/MeOH).

Workup

  1. temperatureTo 10 minutes ice-bath cooled
  2. additionwas added
  3. temperaturethe reaction mixture was refluxed for 6 hrs
  4. temperaturemixture refluxed for 15 min
  5. filtrationparticipate was filtered off
  6. customOrganics were evaporated

Sources & evidence

ORD record
ord-0000bc74669d47b0bece25c41bc907a9
Source dataset
uspto-grants-2016_02
Patent number
US09249127B2

Reaction notes

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