Lithium Hydroxide → HCID 91570370, compound

HRID 2228556Notes

Reaction equation

HRID 2228556 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:33]=[CH:34][CH:35]=1)[C:6]([NH:8][C:9]1[C:10]([NH:21][C:22](=[O:32])[C:23]2[CH:28]=[CH:27][C:26]([CH:29]([CH3:31])[CH3:30])=[CH:25][CH:24]=2)=[CH:11][C:12]([CH2:15][C:16]([O:18]CC)=[O:17])=[CH:13][CH:14]=1)=[O:7])#[N:2].[Li+].[OH-]>C1COCC1.CO.CCOCC>[C:1]([C:3]1[CH:4]=[C:5]([CH:33]=[CH:34][CH:35]=1)[C:6]([NH:8][C:9]1[C:10]([NH:21][C:22](=[O:32])[C:23]2[CH:24]=[CH:25][C:26]([CH:29]([CH3:31])[CH3:30])=[CH:27][CH:28]=2)=[CH:11][C:12]([CH2:15][C:16]([OH:18])=[O:17])=[CH:13][CH:14]=1)=[O:7])#[N:2]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 54417305HCID 54417305, compound

Product 1

HCID 91570370HCID 91570370, compoundYield 99.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of N1-(3-cyanobenzoyl)-N2-(4-isopropylbenzoyl)-4-(ethoxycarbonyl-methyl)-1,2-benzenediamine (1.41 g, 3.00 mmol) in THF (30 mL) and MeOH (10 mL) was added 1 M LiOH (10 mL) and stirred for 2.5 h. The reaction was diluted with Et2O (300 mL) and washed with 1N HCl (40 mL) and H20 (40 mL). The organic layer was concentrated to give the title compound as a pale yellow solid (1.32 g, quant.); IR(KBr): 1326, 1515, 1625, 1672, 3326 cm−1; NMR(300 MHz, DMSO-d6): 1.19 (d, 6H, J=6.9 Hz); 2.97 (m, 1H); 3.65 (s, 2H); 7.12 (d, 1H, J=8.1 Hz); 7.35 (d, 2H, J=7.8 Hz); 7.49 (d, 1H, J=8.1 Hz); 7.54 (s, 1H); 7.71 (t, 1H, J=8.0 Hz); 7.86 (d, 2H, J=7.8 Hz); 8.02 (d, 1H, J=7.2 Hz); 8.22 (d, 1H, J=8.4 Hz); 8.34 (s, 1H); 9.96 (s, 1H); 10.27 (s, 1H); MS(FD): 441.0.

Workup

  1. washwashed with 1N HCl (40 mL) and H20 (40 mL)
  2. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-18c5dd53cd4d44e09c1505055705745d
Source dataset
uspto-grants-2002_07
Patent number
US06417200B1

Reaction notes

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