Hydrochloric Acid → N-(2-fluoro-5-hydroxyphenyl)-3,4,5,6-tetrahydrophthalimide

HRID 1284605Notes

Reaction equation

HRID 1284605 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](N)=[CH:4][C:3]=1[N:9]1[C:13](=[O:14])[C:12]2[CH2:15][CH2:16][CH2:17][CH2:18][C:11]=2[C:10]1=[O:19].N([O-])=[O:21].[Na+].S(=O)(=O)(O)O.Cl>O.C(O)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:21])=[CH:4][C:3]=1[N:9]1[C:13](=[O:14])[C:12]2[CH2:15][CH2:16][CH2:17][CH2:18][C:11]=2[C:10]1=[O:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 10332826N-(2-fluoro-5-aminophenyl)-3,4,5,6-tetrahydrophthalimideHCID 23668193Sodium Nitrite

Product 1

HCID 13519181N-(2-fluoro-5-hydroxyphenyl)-3,4,5,6-tetrahydrophthalimide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

The compound (VI) is prepared by reacting the compound (VIII) with a 1 to 2 equivalent amount of sodium nitrite in a solvent (e.g. sulfuric acid, hydrochloric acid, acetic acid, water) at a temperature of 0° to 20° C. for a period of 5 minutes to 5 hours to obtain its diazonium salt, followed by hydrolysis of the diazonium salt in dilute sulfuric acid at a temperature of 20° to 100° C. In the hydrolysis, a copper compound such as cuprous oxide or cupric nitrate may be used in place of dilute sulfuric acid.

Workup

  1. customat a temperature of 0° to 20° C.
  2. customof 5 minutes to 5 hours

Sources & evidence

ORD record
ord-54e995ccd5514c3dbe04cb44a4ba4a31
Source dataset
uspto-grants-1986_01
Patent number
US04563535

Reaction notes

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