Nitric Acid → HCID 20772336, compound

HRID 1814776Notes

Reaction equation

HRID 1814776 reaction equation
[N+:1]([O-:4])(O)=[O:2].FC(F)(F)C(O)=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[CH3:25][O:26][C:27](=[O:42])[NH:28][CH:29]1[CH2:37][C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]1[O:38][C:39](=[O:41])[CH3:40].C(=O)(O)N>C(Cl)Cl.O>[CH3:25][O:26][C:27](=[O:42])[NH:28][CH:29]1[CH2:37][C:36]2[C:31](=[CH:32][C:33]([N+:1]([O-:4])=[O:2])=[CH:34][CH:35]=2)[CH:30]1[O:38][C:39](=[O:41])[CH3:40]

Participants

7

Reactant 4

HCID 944Nitric AcidHCID 6422Trifluoroacetic acidHCID 9845Trifluoroacetic anhydrideHCID 86588387HCID 86588387, compound

Product 1

HCID 20772336HCID 20772336, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To 90% HNO3 (55.1 mL, 0.8 mol) under nitrogen at −30° C. is added 100 mL of trifluoroacetic acid followed by the addition of trifluoroacetic anhydride (100 g, 0.476 mol) over 5 minutes. The above carbamate (1-acetyloxy-indan-2-yl)-carbamic acid methyl ester (1S-trans)) (20.0 g, 0.08 mol) in 34 mL of methylene chloride is added slowly (over 90 min.) keeping the temperature between −30 and −35° C. The reaction is worked up by adding 100 mL of water and warmed to 0° C. to give two layers. The layers are separated and the aqueous layer extracted with methylene chloride. The combined organic extracts are washed with 100 mL of water (pH is adjusted to 8.5 with sodium bicarbonate), and with cold water. The organic layer is dried over MgSO4, filtered and evaporated to give crude product. The crude product is crystallized from ethyl acetate and further precipitated by the addition of heptane to give (1-acetyloxy-6-nitro-indan-2-yl)-carbamic acid methyl ester (1S-trans); mp 164-167° C.

Workup

  1. customthe temperature between −30 and −35° C
  2. customto give two layers
  3. customThe layers are separated
  4. extractionthe aqueous layer extracted with methylene chloride
  5. washThe combined organic extracts are washed with 100 mL of water (pH is adjusted to 8.5 with sodium bicarbonate)
  6. dry with materialThe organic layer is dried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customto give crude product
  10. customThe crude product is crystallized from ethyl acetate
  11. customfurther precipitated by the addition of heptane

Sources & evidence

ORD record
ord-d04d809450324b62867ff90e985fd813
Source dataset
uspto-grants-2005_04
Patent number
US06878707B2

Reaction notes

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