Hydrochloric Acid → Aminoindanol

HRID 1861136Notes

Reaction equation

HRID 1861136 reaction equation
[NH2:1][C@@H:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@@H:3]1O.[OH:12]C1CC2C(=CC=CC=2)C1=NO.Cl>CO.[Pd]>[NH2:1][C:2]1([OH:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 2725045(1R,2S)-(+)-cis-1-Amino-2-indanolHCID 713473561-(Hydroxyimino)-2,3-dihydro-1H-inden-2-ol

Product 1

HCID 19357388Aminoindanol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

U.S. Pat. No. 6,057,479 (Mitamura et al.) discloses the preparation of cis-1-amino-2-indanol by the catalytic hydrogenation of 2-hydroxy-1-indanone oxime in methanol. Example 21 of U.S. '479 discloses the hydrogenation in the presence of Pd black and HCl to give an aminoindanol product having a cis/trans selectivity of 95.5:4.5. Examples 22-23 report similar results for analogous hydrogenations using Pd/C and Pd/alumina. Example 24 discloses an analogous hydrogenation using Pd black and aqueous HBr to provide 1-amino-2-indanol product with a cis/trans ratio of 95.6:4.4. Results substantially the same as in Example 24 are also reported in Kajiro et al., SYNLETT 1998, p. 51.

Sources & evidence

ORD record
ord-15416dc3f5534d26b627c90dbfc373fd
Source dataset
uspto-grants-2003_03
Patent number
US06531617B2

Reaction notes

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