HCID 86695865, compound → HCID 86695866, compound

HRID 338753Notes

Reaction equation

HRID 338753 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:19][CH2:18][C:17]3[C:12](=[CH:13][N:14]=[CH:15][CH:16]=3)[CH2:11]2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>[Pd]>[CH2:11]1[C:12]2[C:17](=[CH:16][CH:15]=[N:14][CH:13]=2)[CH2:18][CH2:19][N:10]1[C:7]1[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 86695865HCID 86695865, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86695866HCID 86695866, compoundYield 108.5%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of 2-(4-nitrophenyl)-1,2,3,4-tetrahydro-2,7-naphthyridine (11.5 g; 0.045 mol) in IMS (230 mL) was hydrogenated under a hydrogen balloon in the presence of 10% Pd/C (1.2 g). After 3.5 hours tlc analysis indicated the reaction was complete. The hydrogen atmosphere was replaced by argon and degassed DCM (100 mL) was added to re-dissolve the precipitated product. The mixture was filtered through Celite and washed through with degassed DCM:IMS (1:1; 200 mL). To the yellow filtrate was quickly added concentrated hydrochloric acid (40 mL) with stirring and a precipitate crashed out after a few seconds. After 10 minutes, the mixture was filtered, washed with 1:1 DCM:IMS then twice with ether. The off-yellow product was dried in vacuo at 50° C. to afford the title compound as a beige solid (11 g) m.p.>220° C. 1H NMR (DMSO-d6) δ: 8.82 (s, 1H), 8.68 (d, J=6.2 Hz, 1H), 7.86 (d, J=5.9 Hz, 1H), 7.26-7.32 (m, 2H), 7.10-7.16 (m, 2H), 4.61 (s, 2H), 3.67 (t, J=5.9 Hz, 2H), 3.17 (t, J=5.7 Hz, 2H)

Workup

  1. customdegassed DCM (100 mL)
  2. additionwas added
  3. dissolutionto re-dissolve the precipitated product
  4. filtrationThe mixture was filtered through Celite
  5. washwashed through with degassed DCM:IMS (1:1; 200 mL)
  6. additionTo the yellow filtrate was quickly added concentrated hydrochloric acid (40 mL)
  7. waita precipitate crashed out after a few seconds
  8. waitAfter 10 minutes
  9. filtrationthe mixture was filtered
  10. washwashed with 1:1 DCM
  11. customThe off-yellow product was dried in vacuo at 50° C.

Sources & evidence

ORD record
ord-47156e37e5b64cf0b566ee1869daa314
Source dataset
uspto-grants-2014_11
Patent number
US08889870B2

Reaction notes

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