Ethanol → HCID 86590038, compound

HRID 1883716Notes

Reaction equation

HRID 1883716 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH:8]([CH2:13][C:14]([OH:16])=[O:15])[CH2:7]2)([O-])=O.C(=O)(O)[O-].[Na+].S(=O)(=O)(O)O.[CH2:27](O)[CH3:28]>S(=O)(=O)(O)O>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH:8]([CH2:13][C:14]([O:16][CH2:27][CH3:28])=[O:15])[CH2:7]2

Participants

6

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 23508324HCID 23508324, compound

Product 1

HCID 86590038HCID 86590038, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

A solution of (5-nitro-indan-2-yl)-acetic acid [2.22 g, Reference Example 9(a)] in ethanol (100 ml) containing sulfuric acid (5 drops) was refluxed for 4 hours, after which HPLC showed only a trace of free acid remaining. The mixture was treated with solid sodium bicarbonate to neutralise the sulfuric acid and then filtered. The filtrate was placed under a nitrogen atmosphere then 10% palladium on carbon (0.14 g) was added. The mixture was stirred rapidly and hydrogen was bubbled through the solution from a balloon. The reaction was monitored by HPLC until reduction was completed (4 hours) when the reaction mixture was filtered through a pad of celite. The filtrate was evaporated to give the title compound (2.16 g) as a dark red oil which was used without further purification.

Workup

  1. temperaturewas refluxed for 4 hours
  2. filtrationfiltered
  3. addition10% palladium on carbon (0.14 g) was added
  4. customhydrogen was bubbled through the solution from a balloon
  5. custom(4 hours) when
  6. filtrationwas filtered through a pad of celite
  7. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-9d53f96a054e48be8a488c55789f7bba
Source dataset
uspto-grants-2004_07
Patent number
US06762199B2

Reaction notes

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