Sodium Hydroxide → 4-(((1,2-Dihydro-3-methyl-1-oxobenzo(f)quinazolin-9-yl)methyl)amino)-2-fluorobenzoic acid

HRID 369776Notes

Reaction equation

HRID 369776 reaction equation
[CH3:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:8]3[CH:13]=[C:14]([CH2:17][NH:18][C:19]4[CH:29]=[CH:28][C:22]([C:23]([O:25]CC)=[O:24])=[C:21]([F:30])[CH:20]=4)[CH:15]=[CH:16][C:7]=3[CH:6]=[CH:5][C:4]=2[N:3]=1.[OH-].[Na+]>CCO>[CH3:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:8]3[CH:13]=[C:14]([CH2:17][NH:18][C:19]4[CH:29]=[CH:28][C:22]([C:23]([OH:25])=[O:24])=[C:21]([F:30])[CH:20]=4)[CH:15]=[CH:16][C:7]=3[CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 135708790HCID 135708790, compound

Product 1

HCID 1357087934-(((1,2-Dihydro-3-methyl-1-oxobenzo(f)quinazolin-9-yl)methyl)amino)-2-fluorobenzoic acidYield 80.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 100 mL 3-necked flask equipped with a magnetic stirrer was charged with 0.200 g of ethyl 4-(((1,2-dihydro-3-methyl-1-oxobenzo(f)quinazolin-9-yl)methyl)amino)-2-fluorobenzoate, 18 mL of 1 N NaOH, and 20 mL of EtOH. After stirring overnight at RT, the solution was concentrated to 20 mL in vacuo and acidified to pH 2.5 by addition of concentrated HCl. The resulting precipitate was collected by vacuum filtration, washed with 15 mL of water, and dried in vacuo to afford 0.15 g (77%) of 4-(((1,2-dihydro-3-methyl-1-oxobenzo(f)quinazolin-9-yl)methyl)amino)-2-fluorobenzoic acid as a white powder, m.p. >250° C.

Workup

  1. customA 100 mL 3-necked flask equipped with a magnetic stirrer
  2. concentrationthe solution was concentrated to 20 mL in vacuo
  3. additionacidified to pH 2.5 by addition of concentrated HCl
  4. filtrationThe resulting precipitate was collected by vacuum filtration
  5. washwashed with 15 mL of water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-77084ecb8a814669b28a626396d26cad
Source dataset
uspto-grants-2000_10
Patent number
US06140100

Reaction notes

Loading…