Sodium Hydroxide → HCID 67307516, compound

HRID 1877449Notes

Reaction equation

[OH-:1].[Na+].C[O:4][C:5]([C:7]1[C:19]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]([C:20]3[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][N:21]=3)[C:11]=2[CH:10]=[CH:9][CH:8]=1)=[O:6]>CO>[C:26]([C:23]1[CH:24]=[CH:25][C:20]([N:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[C:7]([C:5]([OH:6])=[O:4])[C:19]=3[C:18]3[C:13]2=[CH:14][CH:15]=[CH:16][CH:17]=3)=[N:21][CH:22]=1)(=[O:1])[NH2:27]

Participants

Conditions

Temperature: 60 °C

Procedure

1.6 ml of 2M sodium hydroxide are added to a solution of 0.33 g of 9-(5-cyanopyridin-2-yl)-9H-carbazole-4-carboxylic acid methyl ester, obtained according to the preceding stage, in 30 ml of methanol, and then the mixture is heated at 60° C. for 2 hours. After a return to ambient temperature, the reaction mixture is concentrated under reduced pressure, and then 20 ml of water and a 1M aqueous solution of HCl are added in order to bring the pH to around 6. The aqueous phase is extracted with 3×100 ml of ethyl acetate, and the organic phases are then combined, dried over magnesium sulphate and concentrated under reduced pressure. 0.24 g of 9-(5-carbamoylpyridin-2-yl)-9H-carbazole-4-carboxylic acid is thus obtained in the form of a rubbery residue, the characteristics of which are the following:

Workup

customobtained
concentrationAfter a return to ambient temperature, the reaction mixture is concentrated under reduced pressure
addition20 ml of water and a 1M aqueous solution of HCl are added in order
extractionThe aqueous phase is extracted with 3×100 ml of ethyl acetate
dry with materialdried over magnesium sulphate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-cd08f0cf44994f5bbc5e538116414d4e
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309721B2

Reaction notes

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