Ammonia → HCID 9925394, compound

HRID 1612053Notes

Reaction equation

HRID 1612053 reaction equation
[CH2:1]([N:8]1[C:20]2[CH:19]=[C:18]3[CH:21]=[CH:22][CH:23]=[CH:24][C:17]3=[C:16]([OH:25])[C:15]=2[C:14]2[C:13]([C:26]([O:28]C)=O)=[CH:12][CH:11]=[CH:10][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:30]#N.N>C1COCC1>[CH2:1]([N:8]1[C:20]2[CH:19]=[C:18]3[CH:21]=[CH:22][CH:23]=[CH:24][C:17]3=[C:16]([OH:25])[C:15]=2[C:14]2[C:13]([C:26]([NH2:30])=[O:28])=[CH:12][CH:11]=[CH:10][C:9]1=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 222Ammonia2×HCID 947NitrogenHCID 23594017HCID 23594017, compound

Product 1

HCID 9925394HCID 9925394, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 5-benzyl-11-hydroxy-5H-benzo[b]carbazole-1-carboxylic acid, methyl ester, (0.229 g, 0.60 mM) in 8 mL THF was placed in an Ace Glass pressure tube (203 mm×38 mm) with a small stirring bar. A N2(g) stream was installed over the solution surface. The pressure tube and reaction solution were cooled to −78° C., and ˜8 mL NH3(l) was condensed into the reaction vessel by introduction of an NH3(g) stream. The pressure tube was sealed with a teflon O-ring screw cap, the resultant orange solution stirred at −78° C. for 10 minutes, then the cooling bath was removed and the reaction solution allowed to warm to ambient temperature behind a blast shield. After 48 h, the pressure tube was re-cooled to −78° C. and the internal NH3(g) pressure was released by careful removal of the Teflon™ cap. The reaction solution was allowed to slowly warm to room temperature while NH3(g) bubbled off, then the solution was concentrated in vacuo to afford 0.22 g (99%) of the title compound 5-benzyl-11-hydroxy-5H-benzo[b]carbazole-1-carboxylic acid amide as a yellowish-green solid (MW 366.42).

Workup

  1. customThe pressure tube and reaction solution
  2. customcap
  3. customthe cooling bath was removed
  4. temperatureto warm to ambient temperature behind a blast shield
  5. waitAfter 48 h
  6. temperaturethe pressure tube was re-cooled to −78° C.
  7. customthe internal NH3(g) pressure was released by careful removal of the Teflon™
  8. customcap
  9. temperatureto slowly warm to room temperature while NH3(g)
  10. custombubbled off
  11. concentrationthe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-33e3e1b7b6f64eaa93a21f5a2e88bc7b
Source dataset
uspto-grants-2006_01
Patent number
US06992100B2

Reaction notes

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