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Pyridine → N-(9,9-dipropyl-2-hydroxy-3-fluorenyl)-2-methoxydibenzofuran-3-carboxamide

HRID 1081530
Notes
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Reaction equation

HRID 1081530 reaction equation
[C:1]([C:4]1[C:5]([O:17][CH3:18])=[CH:6][C:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[O:9][C:8]=2[CH:16]=1)([OH:3])=O.S(Cl)(Cl)=O.[NH2:23][C:24]1[C:25]([OH:43])=[CH:26][C:27]2[C:28]([CH2:40][CH2:41][CH3:42])([CH2:37][CH2:38][CH3:39])[C:29]3[C:34]([C:35]=2[CH:36]=1)=[CH:33][CH:32]=[CH:31][CH:30]=3.N1C=CC=CC=1>O1CCCC1.CN1CCCC1=O>[CH2:40]([C:28]1([CH2:37][CH2:38][CH3:39])[C:27]2[CH:26]=[C:25]([OH:43])[C:24]([NH:23][C:1]([C:4]3[C:5]([O:17][CH3:18])=[CH:6][C:7]4[C:11]5[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=5[O:9][C:8]=4[CH:16]=3)=[O:3])=[CH:36][C:35]=2[C:34]2[C:29]1=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:41][CH3:42]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 458266HCID 458266, compoundHCID 10540797HCID 10540797, compound

Product 1

HCID 10696906N-(9,9-dipropyl-2-hydroxy-3-fluorenyl)-2-methoxydibenzofuran-3-carboxamideYield 72.1%

Reagents, catalysts & solvents 2

HCID 8028
Tetrahydrofuran
Solvent
2×
HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Into a 250 ml, 2-necked, round-bottomed flask, equipped with magnetic stirring, nitrogen inlet, and reflux condenser, were placed 6.98 g (28.8 mmole) of 3-carboxy-2-methoxydibenzofuran, 50 ml of dry tetrahydrofuran, 2.20 ml (30.2 mmole) of thionyl chloride, and 0.1 to 0.2 ml of N-methylpyrrolidinone. The mixture was refluxed for 2.5 hours and then allowed to cool to room temperature. Meanwhile, into a 3-necked, 500 ml, round bottomed flask, equipped with magnetic stirring, pressure-equalizing addition funnel, nitrogen inlet, and thermometer, were placed 8.99 g (30.2 mmole) of 3-amino-9,9-dipropyl-2-hydroxyfluorene, 50 ml dry tetrahydrofuran, and 4.77 ml (60.4 mole) of pyridine. To this solution was added the cooled acid chloride over several minutes, resulting in an exotherm and the formation of a precipitate. The mixture was stirred for an additional 1 hour, quenched by pouring into 400 ml of water, and made acidic (pH ≈1). The solid was collected by vacuum filtration, washed with water, slurried in 200 ml of methanol, refiltered, and washed with an additional 100 ml of methanol, resulting in a yellow solid. After drying obtained 10.5 g (70%) of N-(9,9-dipropyl-2-hydroxy-3-fluorenyl)-2-methoxydibenzofuran-3-carboxamide, mp 252°-255°.

Workup

  1. customInto a 250 ml, 2-necked, round-bottomed flask, equipped with magnetic stirring, nitrogen inlet
  2. temperaturereflux condenser
  3. temperatureThe mixture was refluxed for 2.5 hours
  4. customMeanwhile, into a 3-necked, 500 ml, round bottomed flask, equipped with magnetic stirring, pressure-equalizing addition funnel, nitrogen inlet
  5. customresulting in an exotherm
  6. customquenched
  7. additionby pouring into 400 ml of water
  8. filtrationThe solid was collected by vacuum filtration
  9. washwashed with water
  10. washwashed with an additional 100 ml of methanol
  11. customresulting in a yellow solid
  12. customAfter drying

Sources & evidence

ORD record
ord-22f97a073ad3408089d5eb06d8e8aab0
Source dataset
uspto-grants-1996_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05587112

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes