Sodium Hydroxide → HCID 178488060, compound

HRID 2367389Notes

Reaction equation

HRID 2367389 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:10])[C:6]([NH2:9])=[CH:7][CH:8]=1.[C:11]1([CH2:17][N:18]2[CH2:23][CH2:22][O:21][CH:20]([C:24](O)=O)[CH2:19]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH-].[Na+]>Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]2[NH:9][C:24]([CH:20]3[O:21][CH2:22][CH2:23][N:18]([CH2:17][C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)[CH2:19]3)=[N:10][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 1534044-Methoxy-o-phenylenediamineHCID 27763534-Benzylmorpholine-2-carboxylic acid

Product 1

HCID 178488060HCID 178488060, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 4-methoxybenzene-1,2-diamine (0.5 g, 2.369 mmol) and 4-(phenylmethyl)-2-morpholinecarboxylic acid (1.221 g, 4.74 mmol) in 6N HCl (10 mL) was stirred at 105° C. overnight. The reaction mixture was neutralized with aqueous NaOH and partitioned between EtOAc (50 mL) and water (50 mL). The organic phase was washed with water (50 mL), dried (MgSO4), and evaporated in vacuo to give the crude product as a black oil. The crude product was added to a silica gel column and was eluted with 90:10 CH2Cl2/CH3OH to afford the title compound (0.6 g). LC-MS (ES) m/z=324 [M+H]+.

Workup

  1. custompartitioned between EtOAc (50 mL) and water (50 mL)
  2. washThe organic phase was washed with water (50 mL)
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo
  5. customto give the crude product as a black oil
  6. washwas eluted with 90:10 CH2Cl2/CH3OH

Sources & evidence

ORD record
ord-2dfb28ee480b402b975529ae2b9e693c
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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