Ammonia → HCID 59300381, compound

HRID 2236554Notes

Reaction equation

HRID 2236554 reaction equation
C([O:3][C:4]([CH2:6][C:7]1[CH:15]=[C:14]([O:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10])=O)C.[NH3:25]>O1CCOCC1>[C:4]([CH2:6][C:7]1[CH:15]=[C:14]([O:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10])(=[O:3])[NH2:25]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 59300386HCID 59300386, compound

Product 1

HCID 59300381HCID 59300381, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-ethoxycarbonylmethyl-4-(2-morpholin-4-yl-ethoxy)-benzoic acid (2.65 g, 10.0 mmole) and saturated ammonia in dioxane (15 mL) in a pressure bottle is stirred and heated using an oil bath at 95° C. overnight. This mixture is cooled and followed by Ic/ms, reaction not complete. The dioxane is evaporated and replaced with 15 mL of 7M ammonia in methanol and heated overnight in a pressure bottle using an oil bath at 70° C., still a small amount of starting material left. The solvent is removed in vacuo and used as is in the next step MS (ESI): m/z 309.3 (M+H).

Workup

  1. temperatureheated
  2. customat 95° C.
  3. customovernight
  4. temperatureThis mixture is cooled
  5. customfollowed by Ic/ms, reaction not complete
  6. customThe dioxane is evaporated
  7. temperatureheated overnight in a pressure bottle
  8. customat 70° C.
  9. waitstill a small amount of starting material left
  10. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-a05de5762c9d48fa99d207ca70af27da
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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