Ammonia → HCID 17972763, compound

HRID 1612062Notes

Reaction equation

HRID 1612062 reaction equation
[CH2:1]([N:8]1[C:20]2[CH:19]=[C:18]3[CH2:21][CH2:22][CH2:23][CH2:24][C:17]3=[C:16]([OH:25])[C:15]=2[C:14]2[C:13]([C:26](OC)=[O:27])=[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[CH2:21][CH2:22][CH2:23][CH2:24][C:17]3=[C:16]([OH:25])[C:15]=2[C:14]2[C:13]([C:26]([NH2:30])=[O:27])=[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 23594016HCID 23594016, compound

Product 1

HCID 17972763HCID 17972763, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 5-benzyl-11-hydroxy-7,8,9,10-tetrahydro-5H-benzo[b]carbazol-1-carboxylic acid, methyl ester, (0.097 g, 0.25 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 brown 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 24 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 0.92 g (quantitative) of the title compound 5-benzyl-11-hydroxy-7,8,9,10-tetrahydro-5H-benzo[b]carbazole-1-carboxylic acid amide as a tan solid (MP 225° C. dec, MW 370.46).

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 24 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-0624ae24ae024da9bccf91e13447dbc3
Source dataset
uspto-grants-2006_01
Patent number
US06992100B2

Reaction notes

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