Sodium Nitrate → HCID 53820630, compound

HRID 597051Notes

Reaction equation

HRID 597051 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]([CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH:5]1[CH3:18])(=[O:3])[CH3:2].[N+:19]([O-])([O-:21])=[O:20].[Na+]>S(=O)(=O)(O)O>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([N+:19]([O-:21])=[O:20])=[CH:10][CH:11]=2)[CH:6]([CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH:5]1[CH3:18])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 24268Sodium NitrateHCID 54175452HCID 54175452, compound

Product 1

HCID 53820630HCID 53820630, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of methyl 1-acetyl-2-methylindolin-3-ylacetate (6.83 g.) in concentrated sulphuric acid (45 ml.) was cooled to 0° C. and a solution of sodium nitrate (2.67 g.) in concentrated sulphuric acid (20 ml.) was added dropwise during 0.5 hr. The mixture was stirred at 0° C. for a further 0.5 hr. and then poured onto ice (300 ml.). The resulting precipitate was filtered and washed well with water. Crystallisation from methanol gave methyl 1-acetyl-2-methyl-5-nitroindolin-3-ylacetate, m.p. 106° C.

Workup

  1. additionand then poured onto ice (300 ml.)
  2. filtrationThe resulting precipitate was filtered
  3. washwashed well with water
  4. customCrystallisation from methanol

Sources & evidence

ORD record
ord-ebb2be95cc854a1aa1d6b5983a516c7a
Source dataset
uspto-grants-1977_03
Patent number
US04012513

Reaction notes

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