Hydrochloric Acid → HCID 86605147, compound

HRID 901989Notes

Reaction equation

HRID 901989 reaction equation
C([NH:8][C@@H:9]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2[O:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:11][C@H:10]1[OH:26])C1C=CC=CC=1.[ClH:27]>C(O)C.[Pd]>[ClH:27].[NH2:8][C@@H:9]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2[O:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:11][C@H:10]1[OH:26]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58646722HCID 58646722, compound

Product 1

HCID 86605147HCID 86605147, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of trans 3-benzylamino-5-carboethoxymethoxy-2-hydroxy-1,2,3,4-tetrahydronaphthalene (10 g) in 95% aqueous ethanol (200 mL) was added dropwise concentrated aqueous hydrochloric acid solution to bring the pH to 6. Addition of 5% palladium on carbon was followed by hydrogenation on a Parr apparatus at 50 psi for 1 day. The mixture was filtered, rinsing the catalyst with 95% aqueous ethanol and methanol. The filtrate was evaporated to yield a residue. The residue was recrystallized from a mixture of methanol and absolute ethanol to provide the title product (5.2 g, m.p. 210-211° C.).

Workup

  1. filtrationThe mixture was filtered
  2. washrinsing the catalyst with 95% aqueous ethanol and methanol
  3. customThe filtrate was evaporated
  4. customto yield a residue
  5. customThe residue was recrystallized from a mixture of methanol and absolute ethanol

Sources & evidence

ORD record
ord-cf1c7013bb824c7094afa52d6abe749e
Source dataset
uspto-grants-2008_04
Patent number
US07365061B2

Reaction notes

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