Water → 5-Chloro-n-aminoindoline

HRID 267233Notes

Reaction equation

HRID 267233 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([N:11]=O)[CH2:6][CH2:5]2.O>[Zn].C(O)(=O)C>[NH2:11][N:7]1[C:8]2[C:4](=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=2)[CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 962WaterHCID 215559775-Chloro-1-nitrosoindoline

Product 1

HCID 203105795-Chloro-n-aminoindoline

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a stirred mixture of 50 g. (0.27 mole) of 5-chloro-1-nitrosoindoline, 80 g. (1.2 mole) of zinc and 250 ml. of water was added over a 45 minute period 100 ml. of glacial acetic acid. The mixture was filtered, the filtrate basified with 50% sodium hydroxide solution and the base-insoluble oil extracted with ether. The combined ether extracts were dried, concentrated and the residual oil distilled. 1-Amino-5-chloroindoline was distilled at 96°-98°C./0.1 mm. The oil solidified on standing at room temperature.

Workup

  1. additionTo a stirred mixture of 50 g
  2. filtrationThe mixture was filtered
  3. extractionthe base-insoluble oil extracted with ether
  4. dry with materialThe combined ether extracts were dried
  5. concentrationconcentrated
  6. distillationthe residual oil distilled
  7. distillation1-Amino-5-chloroindoline was distilled at 96°-98°C./0.1 mm
  8. customon standing at room temperature

Sources & evidence

ORD record
ord-8c72a6fe16d44bf391bcb14707a47ea4
Source dataset
uspto-grants-1976_03
Patent number
US03941806

Reaction notes

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