Hydrochloric Acid → HCID 605978, compound

HRID 1168419Notes

Reaction equation

HRID 1168419 reaction equation
C([NH:4][C:5]1[C:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[CH:8]=[CH:7][C:6]=1[N+:15]([O-:17])=[O:16])(=O)C.[OH-].[Na+].Cl>C(COC)OC>[NH2:4][C:5]1[C:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[CH:8]=[CH:7][C:6]=1[N+:15]([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22992373HCID 22992373, compound

Product 1

HCID 605978HCID 605978, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

1-(Acetylamino)-2-nitro-5,6,7,8-tetrahydronaphtalene (2.5 g; 10.7 mmol) was suspended in a mixture of dimethoxyethane (30 ml) and aqueous sodium hydroxide (32 ml, 1 M). The mixture was heated to reflux for 2 hours. After cooling two volumes of ice-water was added, and the mixture was neutralised by addition of hydrochloric acid (32 ml, 1 M). The product was filtered off, washed with water and air-dried to yield 1-amino-2-nitro-5,6,7,8-tetrahydronaphtalene (1.95 g, 95%). This product (1.92 g; 10.0 mmol) was dissolved in ethanol and hydrogenated at ambient pressure using Pd (5% on activated carbon) as the catalyst. When the hydrogen uptake had ceased, the mixture was filtered through celite and the filtrate was evaporated to dryness to leave 1,2-diamino-5,6,7,8-tetrahydronaphtalene (1.55 g, 96%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 hours
  3. additionwas added
  4. filtrationThe product was filtered off
  5. washwashed with water
  6. customair-dried

Sources & evidence

ORD record
ord-8674000fcc5c49b488ea491579182fc4
Source dataset
uspto-grants-2003_09
Patent number
US06624186B2

Reaction notes

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