Sodium Hydroxide → HCID 13823533, compound

HRID 1906513Notes

Reaction equation

HRID 1906513 reaction equation
[OH-:1].[Na+].[CH3:3][C:4]([NH:7][CH2:8][CH:9]([OH:28])[CH2:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]#[C:19][C:20]1[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=1)([CH3:6])[CH3:5]>C(O)C>[CH3:6][C:4]([NH:7][CH2:8][CH:9]([OH:28])[CH2:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]#[C:19][C:20]1[CH:27]=[CH:26][C:23]([C:24]([NH2:25])=[O:1])=[CH:22][CH:21]=1)([CH3:3])[CH3:5]

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 13823532HCID 13823532, compound

Product 1

HCID 13823533HCID 13823533, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 11.5 ml (31.5 mmoles) of 3N NaOH solution was added to a solution of 5.8 g (15.3 m moles) of 4-[2-[3-[(1,1-dimethylethyl)amino]-2-hydroxypropoxy]phenylethynyl]benzonitrile, the product of Example 14 in 50 ml of 95% ethanol. The mixture was heated under reflux for 30 min. The solution of 25 ml of 95% ethanol and 5.0 ml of 3N aqueous NaOH was added. The mixture was heated under reflux for 15 min. The solution was cooled and the solid collected by filtration. The solid was recrystallized from 95% ethanol to give 4.38 g of 4-[[2-[3-[(1,1-dimethylethyl)amino]-2-hydroxypropoxy]phenyl]ethynyl]benzamide, mp 199°-201° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 30 min
  3. temperatureThe mixture was heated
  4. temperatureunder reflux for 15 min
  5. temperatureThe solution was cooled
  6. filtrationthe solid collected by filtration
  7. customThe solid was recrystallized from 95% ethanol

Sources & evidence

ORD record
ord-d5d3dcb730cb460aae3104b38ac6c0f6
Source dataset
uspto-grants-1987_03
Patent number
US04652584

Reaction notes

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