Hydrochloric Acid → HCID 136335641, compound

HRID 127567Notes

Reaction equation

HRID 127567 reaction equation
[N+:1]([C:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:8](=O)[C:7]2[CH:16]=[CH:17][CH:18]=[CH:19][C:6]=2[CH:5]=1)([O-])=[O:2].Cl.[NH2:21][OH:22].Cl>N1C=CC=CC=1>[N:21](=[C:8]1[C:7]2[CH:16]=[CH:17][CH:18]=[CH:19][C:6]=2[CH2:5][C:4](=[N:1][OH:2])[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]1=2)[OH:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 443297Hydroxyamine hydrochlorideHCID 12747240HCID 12747240, compound

Product 1

HCID 136335641HCID 136335641, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A mixture of 50.00 g of the product mixture from the stannous chloride reduction of 10-nitro-5H-dibenzo[a,d]cyclohepten-5-one and 62.61 g (0.901 mol) of hydroxylamine hydrochloride in 500 ml of pyridine was refluxed for 6 hr, poured into 3000 ml of ice water and 100 ml of conc. HCl, and extracted with CH2Cl2. The extracts were washed with brine, dried, treated with activated charcoal, filtered, and concentrated in vacuo to give a solid suspended in pyridine. The solid was removed by filtration and the pyridine treated as above to give a white solid. The solids were combined giving 44.09 g of 5,10-dioximino-10,11-dihydro-5H-dibenzo[a,d]cycloheptene as a white solid which had incorporated pyridine. The pyridine could not be removed by heating, high vacuum, or recrystallization: mp 220°-221°; NMR (DMSO-d6 /TMS) δ 11.62 (s, 1H, =NOH), 11.57 (s, 1H, =NOH), 7.50-7.00 (m, 8H, arom), and 3.97 (br s, 2H, benzylic); IR (CHCl3) 2.79, 3.34, 6.33, 6.99, 8.20, 8.34, 9.39, 9.74, 10.09, 10.79, 12.65 and 14.34μ.

Workup

  1. temperaturewas refluxed for 6 hr
  2. extractionextracted with CH2Cl2
  3. washThe extracts were washed with brine
  4. customdried
  5. additiontreated with activated charcoal
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a solid
  9. customThe solid was removed by filtration
  10. additionthe pyridine treated as above
  11. customto give a white solid

Sources & evidence

ORD record
ord-cf76da4abd5f4759a2252aaa20b52bdc
Source dataset
uspto-grants-1981_03
Patent number
US04256742

Reaction notes

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