Hydrochloric Acid → HCID 24851307, compound

HRID 1401389Notes

Reaction equation

HRID 1401389 reaction equation
[C:1]1([CH:7]=[CH:8][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(NCC)C.[N+:22]([CH3:25])([O-:24])=[O:23].Cl.CC[OH:29]>>[OH:29][C:14]1[CH:15]=[CH:16][C:11]([C:9](=[O:10])[CH2:8][CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:25][N+:22]([O-:24])=[O:23])=[CH:12][CH:13]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 6375NitromethaneHCID 7189CinnamoylbenzeneHCID 8021Diethylamine

Product 1

HCID 24851307HCID 24851307, compoundYield 73%

Procedure

A solution of 1-(4-hydroxyphenyl)-3-phenylpropenone 3 (9 mmol) in EtOH (15 mL) was treated with diethylamine (4.6 mL, 45 mmol) and nitromethane (4.8 mL, 90 mmol) and heated under reflux for 16 h. The solution was cooled and acidified with 4 M HCl, partitioned between EtOAc (50 mL) and H2O (50 mL). The organic layer was separated, dried over sodium sulfate and evaporated under reduced pressure. The residue was stirred in cold Et2O (30 mL) for 10 min and filtered to give the product 4 as a colorless solid (1.84 g, 73%), m.p. 112-113° C. (MeOH). 1H NMR (300 MHz, CDCl3): δ 7.86 (d, J=8.5 Hz, 2H), 7.35-7.26 (m, 5H), 6.85 (d, J=8.5, 2H), 5.44 (s, 1H), 4.86-4.80 (m, 1H), 4.64-4.71 (m, 1H), 4.25-4.16 (m, 1H), 3.46-3.31 (m, 2H). 13C NMR (125 MHz, CDCl3): δ 195.3, 160.3, 139.2, 130.6, 129.6, 129.0, 127.8, 127.4, 115.4, 79.6, 41.1, 39.4. IR (KBr disc): 3427, 1646 cm−1. ES-MS: m/z 284.1 [M−H]− HRMS [M+Na]+: 308.0887, C16H15NNaO4+ requires 308.0899.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 16 h
  3. temperatureThe solution was cooled
  4. custompartitioned between EtOAc (50 mL) and H2O (50 mL)
  5. customThe organic layer was separated
  6. dry with materialdried over sodium sulfate
  7. customevaporated under reduced pressure
  8. filtrationfiltered

Sources & evidence

ORD record
ord-faea87ee53ec4fa0be162b53ba0d3a4e
Source dataset
uspto-grants-2014_12
Patent number
US08907107B2

Reaction notes

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