Lithium Hydroxide → HCID 91570370, compound

HRID 1839443Notes

Reaction equation

HRID 1839443 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 H2O (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 H2O (40 mL)
  2. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-a97597b6f6a041058d3cfbf04f5648d3
Source dataset
uspto-grants-2004_01
Patent number
US06677369B2

Reaction notes

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