HCID 21824876, compound → HCID 57437983, compound

HRID 1788002Notes

Reaction equation

HRID 1788002 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][C:3]=1[C:4]#[N:5].[N:18]([O-])=O.[Na+]>Cl.O>[CH2:11]([O:10][C:7]1[CH:6]=[C:3]2[C:2](=[CH:9][CH:8]=1)[NH:1][N:5]=[C:4]2[NH2:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 21824876HCID 21824876, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 57437983HCID 57437983, compoundYield 109.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Procedure

To an ice-cooled suspension of 63.27 g (0.282 mol) of 2-amino-5-(benzyloxy)benzonitrile in 500 ml of concentrated hydrochloric acid, a solution of 23.32 g (0.338 mol) of sodium nitrite in 75 ml of water was added dropwise. After 2 hours the cold suspension was added dropwise to a preformed solution of 509.25 g (2.26 mol) of stannous chloride in 380 ml of concentrated HCl, at 2° C. After 3 hours the cold suspension was filtered and the moist solid was treated with 1.8 l of boiling water and 300 ml of ethanol 950 for 30 min. The hot cloudy solution was clarified by filtration through a cloth filter. The liquors were concentrated to eliminate ethanol and treated dropwise with 0.35 l of 35% NaOH at 4° C. The solid was filtered off and dried under vacuum at 50° C.: 73.82 g of product were obtained as light brown solid. mp=193-195° C. HPLC r.t. 4.7 [M]+=240 [2M+H]+=479

Workup

  1. filtrationAfter 3 hours the cold suspension was filtered
  2. additionthe moist solid was treated with 1.8 l of boiling water and 300 ml of ethanol 950 for 30 min
  3. filtrationThe hot cloudy solution was clarified by filtration through a cloth
  4. filtrationfilter
  5. concentrationThe liquors were concentrated
  6. additiontreated dropwise with 0.35 l of 35% NaOH at 4° C
  7. filtrationThe solid was filtered off
  8. customdried under vacuum at 50° C.

Sources & evidence

ORD record
ord-848ed8065e9447ae95d31be90cddff73
Source dataset
uspto-grants-2009_03
Patent number
US07511136B2

Reaction notes

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