Hydrochloric Acid → HCID 11596091, compound

HRID 1883560Notes

Reaction equation

HRID 1883560 reaction equation
C1(C[O:8][CH2:9][CH2:10]/[CH:11]=[CH:12]\[C:13]2[N:14]=[CH:15][N:16]([C:18]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:17]=2)C=CC=CC=1.Cl>C(O)C.[Pd]>[C:31]1([C:18]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:16]2[CH:17]=[C:13]([CH2:12][CH2:11][CH2:10][CH2:9][OH:8])[N:14]=[CH:15]2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59032668HCID 59032668, compound

Product 1

HCID 11596091HCID 11596091, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of the olefinic ether (17) (18.27 g, 38.8 mmol) in anhydrous ethanol (350 mL), 1.0M ethereal hydrochloric acid (38.8 mL, 38.8 mmol) and 10% palladium-on-carbon catalyst was hydrogenated at 48 psi for 30 min. on a Parr shaker. It was then filtered through celite and the filter cake was washed with methanol. The combined filtrate and washings were concentrated and dried under high vacuum to obtain the title compound (18) as an off-white solid. MP 144-146° C.

Workup

  1. filtrationIt was then filtered through celite
  2. washthe filter cake was washed with methanol
  3. concentrationThe combined filtrate and washings were concentrated
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-d5e573479c264db784f053b416ea5f93
Source dataset
uspto-grants-2004_07
Patent number
US06762186B2

Reaction notes

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