Sodium Carbonate → 8-Amino-1-tetralone

HRID 560131Notes

Reaction equation

HRID 560131 reaction equation
[O:1]=[C:2]1[C:11]2[C:10]([NH:12]C(=O)C)=[CH:9][CH:8]=[CH:7][C:6]=2[CH2:5][CH2:4][CH2:3]1.C([O-])([O-])=O.[Na+].[Na+].[OH-].[Na+]>Cl>[NH2:12][C:10]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:11]=1[C:2](=[O:1])[CH2:3][CH2:4][CH2:5]2

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 12119265N-(8-Oxo-5,6,7,8-tetrahydronaphthalen-1-YL)acetamide

Product 1

HCID 114009428-Amino-1-tetraloneYield 56%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

The amide (Intermediate J2, 4.12 g, 20.3 mmol) was heated at 90 EC in 6N HCl (140 mL) for 3 h. The mixture was cooled to rt and Na2CO3 was added in small portions followed by addition of 2N NaOH until the mixture was at pH 8. The aqueous layer was extracted with EtOAc and the organic fractions were combined, washed with brine, dried, filtered and concentrated to give 8-amino-3,4-dihydro-2H-naphthalen-1-one (Intermediate J3) as a dark red solid 1.82 g (56%).

Workup

  1. extractionThe aqueous layer was extracted with EtOAc
  2. washwashed with brine
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-afa1d4fc04cb4e8481eb24a670ff3dbc
Source dataset
uspto-grants-2011_11
Patent number
US08063086B2

Reaction notes

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