Hydrochloric Acid → 4,6-Diaminoresorcinol Dihydrochloride

HRID 278537

반응식

HRID 278537 반응식
[N+:1]([C:4]1[CH:10]=[C:9]([N+:11]([O-])=O)[C:7]([OH:8])=[CH:6][C:5]=1[OH:14])([O-])=O.CO.CC1C2COC(=O)C=2C(O[C@@H]2O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]2O)=C(C/C=C(/CCC(O)=O)\C)C=1OC.[ClH:52]>O.[C].[Pd]>[ClH:52].[ClH:52].[NH2:1][C:4]1[CH:10]=[C:9]([NH2:11])[C:7]([OH:8])=[CH:6][C:5]=1[OH:14]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 611584,6-DinitroresorcinolHCID 6442661Mycophenolic acid glucuronide

생성물 1

HCID 27336484,6-Diaminoresorcinol Dihydrochloride수율 46.4%

시약·촉매·용매 2

HCID 178418390HCID 178418390, 화합물촉매HCID 962Water용매

실험 절차

30 g of crude 4,6-dinitroresorcin were recrystallized in 1,500 g of ethanol to obtain 24.1 g of purified 4,6-dinitroresorcin. Next, 4.0 g of this purified 4,6-dinitroresorcin were added to methanol, and 0.0396 g of 5% palladium carbon (a 50% wet product) was then added thereto, followed by hydrogenation at 60° C. under an average hydrogen pressure of 0.8 MPaG. The reaction mass was poured into a 5% aqueous hydrochloric acid solution containing 6,000 ppm of stannous chloride, and then filtered to remove the catalyst. Afterward, analysis was carried out by HPLC, and it was confirmed that desired 4,6-diaminoresorcin was produced in a yield of 96.2 mol %. The solvent was removed from the filtrate by an evaporator to obtain the crystals of crude 4,6-dinitroresorcin. The crystals were dissolved in 21.3 g of water containing 0.32 g of stannous chloride, and 0.2 g of activated carbon was added to the solution. Thereafter, the solution was stirred for 30 minutes and then filtered to remove the activated carbon. When 16.0 g of 36% hydrochloric acid were gradually added dropwise to the filtrate, the gradual deposition of crystals was observed. The crystals were collected by filtration and then dried at 50° C. under reduced pressure to obtain 3.03 g (yield=46.4%) of 4,6-diaminoresorcin dihydrochloride.

후처리

  1. additionwas then added
  2. customfollowed by hydrogenation at 60° C. under an average hydrogen
  3. filtrationfiltered
  4. customto remove the catalyst
  5. customwas produced in a yield of 96.2 mol %
  6. customThe solvent was removed from the filtrate by an evaporator
  7. customto obtain the crystals of crude 4,6-dinitroresorcin
  8. additionwas added to the solution
  9. filtrationfiltered
  10. customto remove the activated carbon
  11. additionWhen 16.0 g of 36% hydrochloric acid were gradually added dropwise to the filtrate
  12. filtrationThe crystals were collected by filtration
  13. customdried at 50° C. under reduced pressure

출처 및 근거

ORD 기록
ord-18aa1592fc404da58c4e07a46e519893
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06359180B1

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