Hydrochloric Acid → HCID 21989382, compound

HRID 2226338Notes

Reaction equation

HRID 2226338 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]23[CH2:28][C:14]4([C:29]5[CH:34]=[CH:33][C:32]([N+:35]([O-])=O)=[CH:31][CH:30]=5)[CH2:15][C:16]([C:19]5[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=5)([CH2:18][C:12]([C:38]5[CH:43]=[CH:42][C:41]([N+:44]([O-])=O)=[CH:40][CH:39]=5)([CH2:13]4)[CH2:11]2)[CH2:17]3)=[CH:6][CH:5]=1)([O-])=O.Cl.Cl[Sn]Cl>C(O)C>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]23[CH2:11][C:12]4([C:38]5[CH:43]=[CH:42][C:41]([NH2:44])=[CH:40][CH:39]=5)[CH2:18][C:16]([C:19]5[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=5)([CH2:15][C:14]([C:29]5[CH:34]=[CH:33][C:32]([NH2:35])=[CH:31][CH:30]=5)([CH2:13]4)[CH2:28]2)[CH2:17]3)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24479Stannous ChlorideHCID 19003877HCID 19003877, compound

Product 1

HCID 21989382HCID 21989382, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 1,3,5,7-tetra(p-nitrophenyl)adamantane (0.62 g, 1 mmol) was added 75 mL of ethyl alcohol followed by 15 mL of concentrated hydrochloric acid. Stannous chloride (SnCl2 --2H2O, 4.1 g, 15 mmol), was added to the mixture. After refluxing for 48 hours, the solvent was evaporated and 15 mL of water was added. The aqueous solution was made basic by adding 3M NaOH and was extracted four times with 50 mL of THF. The solvent was evaporated and crude 1,3,5,7-tetra(4-aminophenyl)adamantane was collected (0.5 g, mmol, >90%). 1H NMR (DMSO-d6, 360 MHz): of 1,3,5,7-tetra(4-aminophenyl)adamantane δ1.82 (s 12H), 4.79 (s 8H), 6.50, 6.52, 7.11, 7.13 (AA'BB', 16H). 13C NMR 37.77 (CH2), 47.64 (C--Ph--NH2), 113.65, 125.18, 137.60, 146.12 (Ph--NH2).

Workup

  1. temperatureAfter refluxing for 48 hours
  2. customthe solvent was evaporated
  3. addition15 mL of water was added
  4. additionby adding 3M NaOH
  5. extractionwas extracted four times with 50 mL of THF
  6. customThe solvent was evaporated
  7. customcrude 1,3,5,7-tetra(4-aminophenyl)adamantane was collected (0.5 g, mmol, >90%)

Sources & evidence

ORD record
ord-cd0949d64a244fecacbc362552e5eb27
Source dataset
uspto-grants-1994_09
Patent number
US05347063

Reaction notes

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