Hydrochloric Acid → HCID 70455271, compound

HRID 905355Notes

Reaction equation

HRID 905355 reaction equation
C(O)C.Cl.[O:5]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH:8]=[CH:7][CH:6]1[CH2:15][C:16]1([Cl:47])[CH:21]=[C:20]([N+:22]([O-])=O)[CH:19]=[CH:18][CH:17]1[O:25][CH:26]1[CH:31]=[CH:30][C:29]([N+:32]([O-])=O)=[CH:28][C:27]1([Cl:46])[CH2:35][CH:36]1[CH:41]=[CH:40][C:39]2[CH:42]=[CH:43][CH:44]=[CH:45][C:38]=2[O:37]1.[OH-].[Na+]>[Fe].O>[O:5]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH:8]=[CH:7][CH:6]1[CH2:15][C:16]1([Cl:47])[CH:21]=[C:20]([NH2:22])[CH:19]=[CH:18][CH:17]1[O:25][CH:26]1[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][C:27]1([Cl:46])[CH2:35][CH:36]1[CH:41]=[CH:40][C:39]2[CH:42]=[CH:43][CH:44]=[CH:45][C:38]=2[O:37]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 86739163HCID 86739163, compound

Product 1

HCID 70455271HCID 70455271, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

Under an argon atmosphere, 22.3 g. electrolyte iron, 64 ml. ethanol and 53.4 ml. water were mixed together. To the resultant stirred mixture was added in one portion 1.88 ml. concentrated hydrochloric acid and the resulting mixture heated to reflux. 4.1 g. of the nitro ether prepared in Example I was added to this hot stirred mixture. The addition was made in portions of near reflux temperatures. The mixture was then refluxed for 30 minutes and 1.26 ml. of 50% sodium hydroxide solution was added. This mixture was filtered while hot through dicalite. The filtrate was concentrated in vacuo and then taken up in 200 ml. of methylene chloride, washed with two 500 ml. portions of water and four 100 ml. portions of saturated sodium carbonate solution. The washed mixture was dried over magnesium sulfate and evaporated in vacuo to yield 34 g. of product having a m.p. of 90°-91° C. The product was identified as the title product by IR and NMR analyses.

Workup

  1. additionwas added in one portion 1.88 ml
  2. additionThe addition
  3. temperatureof near reflux temperatures
  4. temperatureThe mixture was then refluxed for 30 minutes
  5. filtrationThis mixture was filtered while hot through dicalite
  6. concentrationThe filtrate was concentrated in vacuo
  7. washof methylene chloride, washed with two 500 ml
  8. dry with materialThe washed mixture was dried over magnesium sulfate
  9. customevaporated in vacuo
  10. customto yield 34 g

Sources & evidence

ORD record
ord-2268a32946f54c079d07f80742ec1ea9
Source dataset
uspto-grants-1983_12
Patent number
US04423237

Reaction notes

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