HCID 19027057, compound → HCID 67833605, compound

HRID 1090085Notes

Reaction equation

HRID 1090085 reaction equation
[C:1]([NH:8][C:9]1[C:18]([N+:19]([O-:21])=O)=[CH:17][C:16]([S:22]([NH:25][C:26]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[O:27])(=[O:24])=[O:23])=[C:15]2[C:10]=1[CH2:11][CH2:12][CH2:13][CH2:14]2)([C:3]([O:5]CC)=O)=[O:2]>C(O)C.[Pt]>[C:26]([NH:25][S:22]([C:16]1[C:15]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=2[C:9]2[NH:8][C:1](=[O:2])[C:3](=[O:5])[N:19]([OH:21])[C:18]=2[CH:17]=1)(=[O:24])=[O:23])([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[O:27]

Participants

4

Reactant 1

HCID 19027057HCID 19027057, compound

Product 1

HCID 67833605HCID 67833605, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 5-ethoxalylamino-8-ethoxalylaminosulfonyl-1,2,3,4-tetrahydro-6-nitronaphthalene (0.61 g, 1.3 mmol) in 100 ml of ethanol was hydrogenated at room temperature and atmospheric pressure in the presence of 60 mg of 5% platinum on carbon. After the theoretical absorption, the mixture was filtered and the filtrate was evaporated to dryness. The crude product (0.51g) was triturated with 50 ml of water, filtered off and then washed with water and a small amount of cold ethanol affording 0.28 g (53%) of the title compound. M.p. 267° C. decomp. (DSC); IR (KBr): 1725 cm-1 ; 1H-NMR (DMSO-d6): 1.23 (t,J=7Hz, 3H, CH3), 1.57-1.93 (m, 4H, 2CH2), 2.63-3.20 (m, 4H, 2CH2), 4.20 (q,J=7Hz, 2H, CH2), 7.98 (s, 1H, ArH), 11.5 (broad s, 1H, NH, only one exchangeable proton could be seen).

Workup

  1. customwas hydrogenated at room temperature
  2. customAfter the theoretical absorption
  3. filtrationthe mixture was filtered
  4. customthe filtrate was evaporated to dryness
  5. customThe crude product (0.51g) was triturated with 50 ml of water
  6. filtrationfiltered off
  7. washwashed with water

Sources & evidence

ORD record
ord-8af1c46aee1948b6ac9a5fd55eccd9d4
Source dataset
uspto-grants-1992_01
Patent number
US05081123

Reaction notes

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