Hydrochloric Acid → Ethyl 3-(4-(2-tetrazolyl)-phenylhydrazino)-4-oxopentanoate

HRID 650232

Reaction equation

HRID 650232 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[N:12]=[N:11][CH:10]=[N:9]2)=[CH:4][CH:3]=1.Cl.[N:14]([O-])=O.[Na+].[C:18]([CH:21](C(=O)C)[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])(=[O:20])[CH3:19]>C(O)C.N1C=CC=CC=1.O>[N:9]1[N:8]([C:5]2[CH:4]=[CH:3][C:2]([NH:1][NH:14][CH:21]([C:18](=[O:20])[CH3:19])[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:7][CH:6]=2)[N:12]=[N:11][CH:10]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 87820Ethyl 3-acetyl-4-oxopentanoateHCID 5716394-(2H-1,2,3,4-tetrazol-2-yl)anilineHCID 23668193Sodium Nitrite

Product 1

HCID 53974079Ethyl 3-(4-(2-tetrazolyl)-phenylhydrazino)-4-oxopentanoate

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 962WaterSolvent3×HCID 1049PyridineSolvent

Procedure

A solution of 1.06 gm. (6.58 mmoles) of 2-(4-aminophenyl)tetrazole in 20 ml. of ethanol and 1.18 ml. of concentrated hydrochloric acid and 10 ml. of water was cooled in an ice bath and treated dropwise with a solution of 500 mg. of sodium nitrite in 10 ml. of water. After the addition of an additional 10 ml. of water, the mixture was stirred for 25 minutes at room temperature. The mixture was then added to a solution of 1.35 gm. (7.2 mmoles) of ethyl 3-acetyl-4-oxopentanoate and 2.66 ml. of pyridine in 15 ml. of ethanol. A solid began to separate. After 1 hour, 10 ml. of 1 M hydrochloric acid was added to adjust the pH to 2-3. An additional 50 ml. of water was added and the solid was collected and washed thoroughly with water and dried. 1.74 g. was obtained.

Workup

  1. additiontreated dropwise with a solution of 500 mg
  2. additionAfter the addition of an additional 10 ml
  3. additionThe mixture was then added to a solution of 1.35 gm
  4. customto separate
  5. additionof 1 M hydrochloric acid was added
  6. additionof water was added
  7. customthe solid was collected
  8. washwashed thoroughly with water
  9. customdried
  10. customwas obtained

Sources & evidence

ORD record
ord-d34bf8f3ed4d489298fa1ff76a6ecde1
Source dataset
uspto-grants-2001_08
Patent number
US06271373B1

Linked notes

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