Hydrochloric Acid → HCID 66995064, compound

HRID 2406294Notes

Reaction equation

HRID 2406294 reaction equation
Cl[C:2]1[N:3]=[C:4]2[C:9](=[C:10]([C:12]34[CH2:19][CH2:18][C:15]([CH:16]=[CH:17]3)=[CH:14][CH2:13]4)[CH:11]=1)[NH:8][CH2:7][CH2:6][CH2:5]2.[NH2:20][NH2:21].Cl>C(O)C>[NH:20]([C:2]1[N:3]=[C:4]2[C:9](=[C:10]([C:12]34[CH2:19][CH2:18][C:15]([CH:16]=[CH:17]3)=[CH:14][CH2:13]4)[CH:11]=1)[NH:8][CH2:7][CH2:6][CH2:5]2)[NH2:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9321Hydrazine2×HCID 86621678HCID 86621678, compound

Product 1

HCID 66995064HCID 66995064, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-Chloro-1,4-ethano-8-phenyl-1,2,3,4-tetrahydro-1,5-naphthyridine (1.03 g) was treated with anhydrous ethanol (10 mL), anhydrous hydrazine (Aldrich, 4.0 mL) and concentrated HCl (0.4 mL). The reaction mixture was then heated in a screw cap pressure tube at 150° C. until LCMS showed complete conversion to the hydrazine (approx. 96 h). The reaction mixture was cooled to ambient temperature, then concentrated under vacuum. The residue was partitioned between chloroform and brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum to give 6-hydrazino-1,4-ethano-8-phenyl-1,2,3,4-tetrahydro-1,5-naphthyridine as a pale yellow solid (0.68 g).

Workup

  1. temperatureThe reaction mixture was then heated in a screw
  2. customcap pressure tube at 150° C. until LCMS
  3. concentrationconcentrated under vacuum
  4. customThe residue was partitioned between chloroform and brine
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f3867900f88f454da4373d3eb4c0b9b7
Source dataset
uspto-grants-2014_08
Patent number
US08809364B2

Reaction notes

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