Hydrochloric Acid → HCID 67854432, compound

HRID 1590663Notes

Reaction equation

HRID 1590663 reaction equation
[N:1]1([C:6]2[CH2:7][CH2:8][C:9]3[CH:10]=[CH:11][C:12]([C:17]([OH:19])=[O:18])=[CH:13][C:14]=3[C:15]=2[CH3:16])[CH:5]=[CH:4][N:3]=[CH:2]1.C(O)C.[ClH:23]>[Pd].C(O)(=O)C>[ClH:23].[N:1]1([CH:6]2[CH:15]([CH3:16])[C:14]3[CH:13]=[C:12]([C:17]([OH:19])=[O:18])[CH:11]=[CH:10][C:9]=3[CH2:8][CH2:7]2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 19767973HCID 19767973, compound

Product 1

HCID 67854432HCID 67854432, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 5,6-dihydro-7(1H-imidazol-1-yl)-8-methyl-2-naphthalenecarboxylic acid (1.5 g), 10% palladium on activated carbon (0.65 g), ethanol 95% (100 ml), glacial acetic acid (30 ml) and concentrated hydrochloric acid (10 ml) is hydrogenated for 8 hours at room temperature in a Parr-Burgess low pressure apparatus at an initial pressure of 50 psi. At the end of this time the theoretical amount of hydrogen has been absorbed. The catalyst is filtered off, washed with 95% ethanol, and the solution is evaporated under reduced pressure. The solid residue is crystallized from 95% ethanol-ethyl ether mixture, giving 1.4 g of 5,6,7,8-tetrahydro-7-(1H-imidazol-1-yl)-8-methyl-2-naphthalenecarboxylic acid hydrochloride.

Workup

  1. customAt the end of this time the theoretical amount of hydrogen has been absorbed
  2. filtrationThe catalyst is filtered off
  3. washwashed with 95% ethanol
  4. customthe solution is evaporated under reduced pressure
  5. customThe solid residue is crystallized from 95% ethanol-ethyl ether mixture

Sources & evidence

ORD record
ord-6ab10598a1f245c58dec1073b397cfa4
Source dataset
uspto-grants-1993_04
Patent number
US05204364

Reaction notes

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