Sodium Hydroxide → HCID 64047272, compound

HRID 571933Notes

Reaction equation

HRID 571933 reaction equation
C([O:3][C:4](=[O:21])[C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[NH:14][CH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)C.[OH-].[Na+]>C(O)C>[N+:11]([C:8]1[CH:9]=[CH:10][C:5]([C:4]([OH:21])=[O:3])=[C:6]([NH:14][CH:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[CH:7]=1)([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66737162HCID 66737162, compound

Product 1

HCID 64047272HCID 64047272, compoundYield 91.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

4-Nitro-2-(tetrahydro-pyran-4-ylamino)-benzoic acid ethyl ester (11.2 g, 38 mmol) was dissolved in 200 mL of ethanol at 60° C. then 2N NaOH was added (40 mL, 80 mmol). The mixture was stirred at 60° C. for 4 hours, then the solvent removed under reduced pressure. The residue was taken-up with 200 mL of water and the mixture brought to acidic pH with 2N HCl (35 mL). The precipitated yellow solid was filtered, washed with plenty of water and dried in oven at 40° C. affording the title compound (9.3 g).

Workup

  1. customthe solvent removed under reduced pressure
  2. filtrationThe precipitated yellow solid was filtered
  3. washwashed with plenty of water
  4. customdried in oven at 40° C.

Sources & evidence

ORD record
ord-319b8e87d9c44382b98016a51c33d6b7
Source dataset
uspto-grants-2015_05
Patent number
US09029356B2

Reaction notes

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