Ammonia → HCID 136378638, compound

HRID 2408991Notes

Reaction equation

HRID 2408991 reaction equation
Cl.[O:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][O:11][C:12]2[C:13]([O:23][CH3:24])=[CH:14][C:15]([NH2:22])=[C:16]([CH:21]=2)[C:17]([O:19]C)=O)[CH2:4][CH2:3]1.O.N.[C:27](#[N:29])[CH3:28]>>[O:2]1[CH2:3][CH2:4][N:5]([CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:21]=[C:16]3[C:15](=[CH:14][C:13]=2[O:23][CH3:24])[N:22]=[C:27]([CH3:28])[NH:29][C:17]3=[O:19])[CH2:6][CH2:7]1

Participants

6

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 962WaterHCID 6342AcetonitrileHCID 11666970Benzoic acid, 2-aMino-4-Methoxy-5-[3-(4-Morpholinyl)propoxy]-, Methyl ester

Product 1

HCID 136378638HCID 136378638, compoundYield 98%

Procedure

Dry HCl gas was passed (until the clear solution observed) to a solution of methyl 5-(3-morpholinopropoxy)-2-amino-4-methoxy-benzoate (1.0 g, 3.0 mmol) in acetonitrile (16 mL) for 30 min at rt. The reaction mixture was refluxed for 3 h and attained to rt. The solution was poured into ice cooled water and basified with ammonia solution. The solution was extracted with EtOAc (3×100 mL) and the combined EtOAc layer was washed water, brine and dried over sodium sulfate. The solution was filtered and evaporated the solvent to give the product as an off-white color solid (1.0 g, 98%), mp 236-238° C. 1H NMR (400 MHz, CDCl3): δ 11.60 (1H, br s), 7.59 (1H, s), 7.08 (1H, s), 4.23 (2H, t, J=6.6 Hz), 3.97 (3H, s), 3.73 (4H, t, J=4.6 Hz), 2.56 (2H, t, J=7.0 Hz), 2.56 (3H, s), 2.48 (4H, t, J=4.4 Hz), 2.09 (2H, pentet, J=6.8 Hz); LC-MS (positive ion mode): m/z 334 (M+H)+.

Workup

  1. customfor 30 min
  2. customat rt
  3. temperatureThe reaction mixture was refluxed for 3 h
  4. customattained to rt
  5. additionThe solution was poured into ice
  6. extractionThe solution was extracted with EtOAc (3×100 mL)
  7. washthe combined EtOAc layer was washed water, brine
  8. dry with materialdried over sodium sulfate
  9. filtrationThe solution was filtered
  10. customevaporated the solvent

Sources & evidence

ORD record
ord-f415b59a44094fc29bc7211e87e3064d
Source dataset
uspto-grants-2014_08
Patent number
US08815879B2

Reaction notes

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