Benzene → HCID 22401339, compound

HRID 260456Notes

Reaction equation

HRID 260456 reaction equation
[CH3:1][N:2]1[C:11]([CH2:12]CC(O)=O)=[C:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:9]2[C:4](=[CH:5][C:6]([CH3:24])=[C:7]([CH3:23])[CH:8]=2)[C:3]1=[O:25].[CH2:26]([N:28](CC)CC)C.[CH:33]1C=[CH:37][CH:36]=[CH:35][CH:34]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[C:56]([O:59][CH2:60][CH3:61])(=[O:58])C>>[CH3:1][N:2]1[C:11]([CH2:12][CH2:26][NH:28][C:56](=[O:58])[O:59][CH2:60][C:61]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[C:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:9]2[C:4](=[CH:5][C:6]([CH3:24])=[C:7]([CH3:23])[CH:8]=2)[C:3]1=[O:25]

Participants

6

Reactant 5

HCID 241BenzeneHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 199401P,P-Diphenylphosphinic azideHCID 22401307HCID 22401307, compound

Product 1

HCID 22401339HCID 22401339, compound

Procedure

To a mixture of 3-(1,2-dihydro-2,6,7-trimethyl-1-oxo-4-phenylisoquinolin-3-yl)propionic acid (Reference Example 10) (650 mg), triethylamine (0.30 ml) and benzene (20 ml) was added, while stirring at room temperature, diphenyl phosphoryl azide (0.30 ml). This mixture was stirred for 30 minutes at room temperature, then for one hour by heating under reflux. To the reaction mixture was added ethyl acetate, which was washed with water, dilute hydrochloric acid, an aqueous solution of sodium hydrogencarbonate and water, successively, followed by drying (MgSO4). The solvent was distilled off to afford the title compound as a colorless crystals (623 mg).

Workup

  1. additionwas added
  2. stirringThis mixture was stirred for 30 minutes at room temperature
  3. temperaturefor one hour by heating
  4. temperatureunder reflux
  5. washwas washed with water, dilute hydrochloric acid
  6. dry with materialby drying (MgSO4)
  7. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-0e1e39057d794a53bc12d161319c77c8
Source dataset
uspto-grants-1996_06
Patent number
US05527811

Reaction notes

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