Ammonia → HCID 67338382, compound

HRID 1671465Notes

Reaction equation

HRID 1671465 reaction equation
[NH2:1][C:2]1[C:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.CO[CH:17](OC)[CH2:18][Br:19].N>S(=O)(=O)(O)O>[Br:19][CH2:18][CH:17]1[NH:1][C:2]2[N:3]=[CH:4][CH:5]=[CH:6][C:7]=2[CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]1=2

Participants

5

Reactant 3

HCID 222AmmoniaHCID 816722-Bromo-1,1-dimethoxyethaneHCID 147619283-Benzylpyridin-2-amine

Product 1

HCID 67338382HCID 67338382, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A mixture of 2-amino-3-benzylpyridine (12.0 g, 65.2 mmol) and bromoacetaldehyde dimethyl acetal (19 g, 112.4 mmol, 1.7 eq.) in a 250 ml round-bottomed flask was treated at room temperature with concentrated sulphuric acid (50 ml) by quick addition. A vigorous exothermic reaction took place. After stirring for one hour the dark mixture was poured on ice (ca. 500 ml). Concentrated ammonia was added to basify the mixture. Extraction was done with ethyl acetate (100 ml) and dichloromethane (2×150 ml). The combined organic layers were dried with Na2SO4. Evaporation under vacuum gave 10-bromomethyl-10,11-dihydro-5H-benzo[e]pyrido[2,3-b]azepine as a brown powder (14 g, 48.6 mmol) in 75% yield. Mass analysis: M+1 289,291 (Br-isotope) major peak.

Workup

  1. customA vigorous exothermic reaction
  2. additionwas poured on ice (ca. 500 ml)
  3. extractionExtraction
  4. dry with materialThe combined organic layers were dried with Na2SO4
  5. customEvaporation under vacuum

Sources & evidence

ORD record
ord-fd706c1a14d04d35b8d5192b5270d316
Source dataset
uspto-grants-2011_08
Patent number
US07994314B2

Reaction notes

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