Ammonium Hydroxide → HCID 12132635, compound

HRID 393253Notes

Reaction equation

HRID 393253 reaction equation
O=P(Cl)(Cl)Cl.[CH3:6][C:7]1([CH3:24])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]([C:21]([NH2:23])=O)[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]1=2.[NH4+].[OH-]>>[C:21]([CH:14]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=2[C:7]([CH3:24])([CH3:6])[C:8]2[C:13]1=[CH:12][CH:11]=[CH:10][CH:9]=2)#[N:23]

Participants

4

Reactant 3

HCID 14923Ammonium Hydroxide2×HCID 24813Phosphorus oxychlorideHCID 4811410-Anthracenecarboxamide, 9,10-dihydro-9,9-dimethyl-

Product 1

HCID 12132635HCID 12132635, compoundYield 87.5%

Procedure

POCl3 (25 mL, 00 mmol) was added to crystalline 10,10-Dimethyl-9,10-dihydroanthracene-9-carboxamide [8] (1.25 g, 4.9 mmol) while stirring. The solution was then heated at reflux (30 min), when TLC showed complete absence of starting material. The solution was then poured into a mixture of crushed ice and NH4OH with vigorous stirring. The solution was stirred for 15 minutes and excess of NH4OH was added to keep the solution alkaline. A solid substance separated out which was extracted with ether (3×50 ml). The combined ether extracts were washed with water, brine, dried (MgSO4) and evaporated under reduced pressure to give an light yellow oil which crystallized immediately. The product obtained was chromatographically pure and recrystallized readily from EtOH to give 1.0 g (86%) of the product as colorless prisms. mp. 91-92° C. 1H NMR (CDCl3)d: 1.54 (s, 3H, CH3), 1.79 (s, 3H, CH3), 5.32 (s, 1H, CH), 7.32-7.68 (m, 8H, Ar—H). 13C NMR (CDCl3)d: 30.22, 30.33, 36.95, 125.77, 127.43, 127.92, 129.28. Anal. Calcd. For (C17H15N): C, H, N.

Workup

  1. temperatureThe solution was then heated
  2. temperatureat reflux (30 min), when TLC
  3. additionwas added
  4. customA solid substance separated out which
  5. extractionwas extracted with ether (3×50 ml)
  6. washThe combined ether extracts were washed with water, brine
  7. dry with materialdried (MgSO4)
  8. customevaporated under reduced pressure
  9. customto give an light yellow oil which
  10. customcrystallized immediately
  11. customThe product obtained
  12. customrecrystallized readily from EtOH

Sources & evidence

ORD record
ord-d738ee193ca841099aae69bf63fe7543
Source dataset
uspto-grants-2004_10
Patent number
US06806283B2

Reaction notes

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