4-Methylmorpholine → Ammonia

HRID 2407669Notes

Reaction equation

HRID 2407669 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[Cl:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][C:9]=1[OH:17].C[N:19]1CCOCC1.[C:25]1([C:31]2[CH:35]=[C:34]([CH2:36][N:37]3[CH2:42][CH2:41][CH:40]([CH2:43][NH2:44])[CH2:39][CH2:38]3)[O:33][N:32]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>ClCCl.C(OCC)(=O)C>[NH3:19].[C:2](=[O:3])([O:4][CH2:5][CH3:6])[O:17][C:9]1[CH:10]=[C:11]([C:12]([NH:44][CH2:43][CH:40]2[CH2:39][CH2:38][N:37]([CH2:36][C:34]3[O:33][N:32]=[C:31]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH:35]=3)[CH2:42][CH2:41]2)=[O:14])[CH:15]=[CH:16][C:8]=1[Cl:7]

Participants

8

Reactant 4

HCID 79724-MethylmorpholineHCID 10928Ethyl chloroformateHCID 1418724-Chloro-3-hydroxybenzoic acidHCID 58504252HCID 58504252, compound

Product 2

HCID 222AmmoniaHCID 66989169HCID 66989169, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl chloroformate (0.029 mL) was added to a 0° C. solution of 4-chloro-3-hydroxybenzoic acid (50 mg) and 4-methylmorpholine (0.092 L) in dichloromethane (2 mL). The reaction was stirred for two hours and then was treated with the compound prepared in Example 9 (79 mg). The reaction was stirred overnight, then diluted with ethyl acetate and washed twice with a saturated aqueous sodium bicarbonate solution. The organic phase was dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:9, then methanol:concentrated aqueous ammonia:ethyl acetate=2:3:95) to obtain the title compound (60 mg) having the following physical data.

Workup

  1. stirringThe reaction was stirred overnight
  2. washwashed twice with a saturated aqueous sodium bicarbonate solution
  3. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (ethyl acetate

Sources & evidence

ORD record
ord-ec10f24ceabe4ba59ba19cfc2cc2727c
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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