HCID 67060326, compound → HCID 67060336, compound

HRID 1625109Notes

Reaction equation

HRID 1625109 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[N:11]1[C:15](=[O:16])[C:14]2([CH2:20][CH2:19][CH2:18][CH2:17]2)[NH:13][C:12]1=[O:21]>CO>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([N:11]2[C:15](=[O:16])[C:14]3([CH2:20][CH2:19][CH2:18][CH2:17]3)[NH:13][C:12]2=[O:21])=[C:2]([Cl:1])[CH:7]=1

Participants

3

Reactant 1

HCID 67060326HCID 67060326, compound

Product 1

HCID 67060336HCID 67060336, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(2-chloro-4-nitrophenyl)-1,3-diazaspiro[4.4]nonane-2,4-dione (268 mg; 0.87 mmol) was stirred in MeOH (15 mL) and catalytic Rainey-Ni (30 mg) was added. The reaction flask evacuated and purged with Ar. The flask was then evacuated and purged with hydrogen (1 atm) via balloon. After vigorous stirring for 1 h, the mixture was filtered through Celite, washed with MeOH and CH2Cl2 and the filtrate was concentrated yielding 3-(4-amino-2-chlorophenyl)-1,3-diazaspiro[4.4]nonane-2,4-dione that was taken to the next step without purification, 1.2.13.

Workup

  1. customThe reaction flask evacuated
  2. custompurged with Ar
  3. customThe flask was then evacuated
  4. custompurged with hydrogen (1 atm) via balloon
  5. filtrationthe mixture was filtered through Celite
  6. washwashed with MeOH and CH2Cl2
  7. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-a37ad1faefeb44409fca45bfd68ec351
Source dataset
uspto-grants-2014_07
Patent number
US08779157B2

Reaction notes

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