2-Benzylamino-7-carbethoxymethoxytetraline hydrochloride → 2-Amino-7-carbethoxymethoxytetraline hydrochloride

HRID 1590359Notes

Reaction equation

HRID 1590359 reaction equation
[ClH:1].C([NH:9][CH:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][C:14]([O:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:15][CH:16]=2)[CH2:11]1)C1C=CC=CC=1>C(O)C.O.[Pd]>[ClH:1].[NH2:9][CH:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][C:14]([O:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:15][CH:16]=2)[CH2:11]1

Participants

5

Reactant 1

HCID 197704852-Benzylamino-7-carbethoxymethoxytetraline hydrochloride

Product 1

HCID 200947462-Amino-7-carbethoxymethoxytetraline hydrochlorideYield 92.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 27 g of 2-benzylamino-7-carbethoxymethoxytetraline hydrochloride, EXAMPLE 1, in 300 ml of 95% ethanol and 25 ml of water, is hydrogenated under ordinary pressure and at temperature of 50° C. by using 3 g of 10% palladium on charcoal as a catalyst. After 3 hours, the mixture is filtered, the residue is taken up twice with 100 ml of absolte ethanol and dried every time. The product so obtained is triturated in 150 ml of acetone, filtered and crystallized from 100 ml of isopropanol to give 19 g of 2-amino-7-carbethoxymethoxytetraline hydrochloride; m.p. 143°-145° C. The product thus obtained may be used for the preparation of the compound of formula (XV) above, in which X is hydrogen and O-R' is a carbethoxymethoxy group (COMPOUND 1), as follows:

Workup

  1. customis hydrogenated under ordinary pressure and at temperature of 50° C.
  2. filtrationthe mixture is filtered
  3. customdried every time
  4. customThe product so obtained
  5. customis triturated in 150 ml of acetone
  6. filtrationfiltered
  7. customcrystallized from 100 ml of isopropanol

Sources & evidence

ORD record
ord-1c22c4dad87c4251a552250b0efc5486
Source dataset
uspto-grants-1993_04
Patent number
US05202466

Reaction notes

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