Methanol → HCID 67581816, compound

HRID 1416994Notes

Reaction equation

HRID 1416994 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[C:5]([F:14])=[CH:4][C:3]=1[N+:15]([O-])=O.[H][H].ClC(O[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=O.[OH-:31].[Na+].[CH3:33][OH:34]>[Pd].O>[C:33]([N:15]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:3]1[CH:2]=[CH:7][C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[C:5]([F:14])[CH:4]=1)([OH:34])=[O:31]

Participants

8

Reactant 5

HCID 887MethanolHCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 10945195HCID 10945195, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 67581816HCID 67581816, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 208.4 g (0.8 mol) of 2-chloro-5-fluoro-4-morpholinonitrobenzene in 516.6 g (0.88 mol) of tri(methyltetraethoxy)amine and 105 g of methanol, together with 18 g of a palladium/activated carbon catalyst (5% by weight of palladium, 50% water-moist) is introduced, at room temperature into a 2000 ml autoclave fitted with gas-dispersion stirrer. The autoclave is closed and rendered inert using nitrogen, and the mixture is reacted at a reaction temperature of from 80 to 100° C. at a hydrogen pressure of from 5 to 30 bar until no more hydrogen is absorbed. After the catalyst has been filtered off with suction, 57.5 g (0.72 mol) of 50% strength NaOH are added to the reaction solution at room temperature, followed by 161.6 g (0.9 mol) of benzyl chloroformate (95% strength). When the addition is complete, the mixture is stirred for a further 15 minutes at 50° C., and 775 g of water and 36 g (0.9 mol) of NaOH are added to the reaction solution/suspension. The solid formed is filtered off with suction, washed with water and then recrystallized from methanol.

Workup

  1. customfitted with gas-dispersion stirrer
  2. customThe autoclave is closed
  3. customis absorbed
  4. filtrationAfter the catalyst has been filtered off with suction, 57.5 g (0.72 mol) of 50% strength NaOH
  5. additionare added to the reaction solution at room temperature
  6. additionWhen the addition
  7. customThe solid formed
  8. filtrationis filtered off with suction
  9. washwashed with water
  10. customrecrystallized from methanol

Sources & evidence

ORD record
ord-ea353b8ef3eb4705bee1bb77d5bd4a89
Source dataset
uspto-grants-1999_06
Patent number
US05917036

Reaction notes

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