Ammonia → HCID 117664236, compound

HRID 2199498Notes

Reaction equation

HRID 2199498 reaction equation
[OH:1][C:2]1[C:11]([CH2:12][CH2:13][C:14]([CH3:16])=[CH2:15])=[C:10]([O:17][CH3:18])[CH:9]=[C:8](/[CH:19]=[CH:20]/[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:3]=1[C:4](OC)=[O:5].[NH3:27]>>[OH:1][C:2]1[C:11]([CH2:12][CH2:13][C:14]([CH3:16])=[CH2:15])=[C:10]([O:17][CH3:18])[CH:9]=[C:8](/[CH:19]=[CH:20]/[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:3]=1[C:4]([NH2:27])=[O:5]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 117664395HCID 117664395, compound

Product 1

HCID 117664236HCID 117664236, compoundYield 92%

Procedure

Dissolve compound 8 (1.0 g, 2.84 mmol) in methanolic ammonia (10%, 10 ml), reflux to react for 4-6h, after completion, pour the solution into ice water, extract the solution with ethyl acetate, desiccate the organic layer over anhydrous magnesium sulfate. Filter and concentrate the solution, redissolve the residue, feed the solution into a chromatographic column, evaporate the solvent in the eluent to obtain a white solid as the target product (0.86 g, 92%). 1H NMR (400 MHz, DMSO-d6): 1.79 (s, 3H), 1.81 (s, 3H), 3.25 (d, J=7.6 Hz, 2H), 3.77 (s, 3H), 5.20 (t, J=7.6 Hz, 1H), 6.68 (s, 1H), 6.80 (d, J=16.0 Hz, 1H), 7.24 (d, J=16.0 Hz, 1H), 79 (t, J=7.6 Hz, 2H), 7.36 (s, 1H), 7.44 (t, J=7.6 Hz, 2H), 7.90 (s, 2H).

Workup

  1. temperaturereflux
  2. customto react for 4-6h
  3. extractionextract the solution with ethyl acetate
  4. filtrationFilter
  5. concentrationconcentrate the solution
  6. dissolutionredissolve the residue
  7. customevaporate the solvent in the eluent

Sources & evidence

ORD record
ord-d80a6a0cde2f4b82ad08b1fdd8188e04
Source dataset
uspto-grants-2016_06
Patent number
US09359298B2

Reaction notes

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