1-(7,8-Dinitro-1,2,4,5-tetrahydro-3H-1,5-methano-3-benzazepin-3-yl)-2,2,2-trifluoroethan-1-one → 1-(7,8-Diamino-1,2,4,5-tetrahydro-3H-1,5-methano-3-benzazepin-3-yl)-2,2,2-trifluoroethan-1-one

HRID 10094Notes

Reaction equation

HRID 10094 reaction equation
[N+:1]([C:4]1[C:14]([N+:15]([O-])=O)=[CH:13][C:12]2[CH:11]3[CH2:18][CH:7]([CH2:8][N:9]([C:19](=[O:24])[C:20]([F:23])([F:22])[F:21])[CH2:10]3)[C:6]=2[CH:5]=1)([O-])=O>CO.[OH-].[OH-].[Pd+2]>[NH2:1][C:4]1[C:14]([NH2:15])=[CH:13][C:12]2[CH:11]3[CH2:18][CH:7]([CH2:8][N:9]([C:19](=[O:24])[C:20]([F:23])([F:21])[F:22])[CH2:10]3)[C:6]=2[CH:5]=1

Participants

4

Reactant 1

HCID 218647441-(7,8-Dinitro-1,2,4,5-tetrahydro-3H-1,5-methano-3-benzazepin-3-yl)-2,2,2-trifluoroethan-1-one

Product 1

HCID 116663681-(7,8-Diamino-1,2,4,5-tetrahydro-3H-1,5-methano-3-benzazepin-3-yl)-2,2,2-trifluoroethan-1-one

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

1-(4,5-Dinitro-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-2,2,2-trifluoro-ethanone (3.0 g, 8.70 mmol) was hydrogenated in methanol (30 ml) under a hydrogen atmosphere (45 psi, or approximately 3 atmospheres) over Pd(OH)2 (300 mg of 20 wt %/C, 10% wt). After 2.5 hours the reaction was filtered through a Celite pad and rinsed with methanol (30 ml). The solution was concentrated to a light brown oil which crystallized (2.42 g, 96%). (TLC 10% methanol/CH2Cl2 Rf 0.56). APCI MS m/e 286.2 [(M+1)+]. M.p. 129–131° C.

Workup

  1. filtrationAfter 2.5 hours the reaction was filtered through a Celite pad
  2. washrinsed with methanol (30 ml)
  3. concentrationThe solution was concentrated to a light brown oil which
  4. customcrystallized (2.42 g, 96%)

Sources & evidence

ORD record
ord-c1e478105e0c4ecf87f53b24e0cc7cb9
Source dataset
uspto-grants-2006_08
Patent number
US07091372B2

Reaction notes

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