Sulfuric Acid → HCID 14122182, compound

HRID 231640Notes

Reaction equation

HRID 231640 reaction equation
[C:1]([C:9]1[CH:14]=[CH:13][C:12]([N:15]=[N:16][C:17]2[CH:22]=[C:21]([C:23]([CH3:31])([CH3:30])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:20]=[C:19]([C:32]([CH3:40])([CH3:39])[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:18]=2[OH:41])=[C:11]([N+:42]([O-])=O)[CH:10]=1)([CH2:4][C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:3])[CH3:2].C1(C)C=CC=CC=1.[OH-].[Na+].S(=O)(=O)(O)O>[Zn].O.C(O)(C)C>[C:1]([C:9]1[CH:14]=[CH:13][C:12]2=[N:15][N:16]([C:17]3[CH:22]=[C:21]([C:23]([CH3:31])([CH3:30])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH:20]=[C:19]([C:32]([CH3:40])([CH3:39])[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[C:18]=3[OH:41])[N:42]=[C:11]2[CH:10]=1)([CH2:4][C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 1140TolueneHCID 14798Sodium HydroxideHCID 135980878HCID 135980878, compound

Product 1

HCID 14122182HCID 14122182, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalyst3×HCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
47 °C

Procedure

To a 300 ml 3-necked flask fitted with a stirrer, thermometer, reflux condenser and nitrogen inlet is charged 31 grams (0.05 mol) of the o-nitroazobenzene intermediate of Example 5 and 100 ml of toluene. To the resulting solution is added 15 ml of isopropanol and 15 ml of water. A nitrogen atmosphere is imposed and 8 grams (0.1 mole) of 50% aqueous sodium hydroxide is added. A flask containing 11.6 grams (0.177 gram-atoms) of zinc is connected to the reaction flask by Gooch rubber tubing and the zinc dust is added portionwise to the reaction mixture in essentially eight (8) equal portions with 15 minute intervals between additions. After all the zinc is added, the mixture is stirred at 47° C. overnight and then heated to reflux for two hours. The mixture is then cooled to 45° C. and acidified with 50 grams of 50% aqueous sulfuric acid.

Workup

  1. customTo a 300 ml 3-necked flask fitted with a stirrer
  2. temperaturethermometer, reflux condenser and nitrogen inlet
  3. temperatureheated
  4. temperatureto reflux for two hours
  5. temperatureThe mixture is then cooled to 45° C.

Sources & evidence

ORD record
ord-e76c3b7f3c3b4481ab6a9820bccbbabf
Source dataset
uspto-grants-1989_07
Patent number
US04847367

Reaction notes

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